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    Building a world-class sales org | Jason Lemkin (SaaStr)

    Rushing through the hiring process can lead to costly mistakes. Take the time to thoroughly vet candidates to reduce turnover and create a successful work environment.

    enFebruary 18, 2024

    About this Episode

    Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss:

    • How far you should go without a salesperson

    • Signs it’s time to hire salespeople

    • Why you need to hire two salespeople

    • How to compensate your salespeople

    • How to interview salespeople

    • When to hire a VP of Sales

    • How to prevent their flaming out

    • How to scale your sales org

    • How to improve the relationship between your sales and product teams

    • Much more

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    Find the full transcript at: https://www.lennyspodcast.com/building-a-world-class-sales-org-jason-lemkin-saastr/

    Where to find Jason Lemkin:

    • X: https://twitter.com/jasonlk

    • LinkedIn: https://www.linkedin.com/in/jasonmlemkin/

    • Website: https://www.saastr.com/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Jason’s background

    (06:18) The importance of sales in B2B businesses

    (11:23) Signs that you should start hiring salespeople

    (14:19) Attributes to look for in early sales reps

    (19:08) Hiring a VP of Sales

    (26:43) The role of a VP of Sales

    (30:06) Interviewing salespeople

    (45:16) Determining sales compensation and quota

    (53:34) Transitioning from 100% commission to a smaller percentage

    (56:58) Indicators of a hard-to-sell product

    (59:39) Scaling the sales organization

    (01:05:26) Understanding sales roles and titles

    (01:10:02) Product involvement in sales, and vice versa

    (01:20:32) Thoughts on product teams taking on P&L responsibilities

    (01:27:23) One thing founders can do to become better at sales

    (01:31:02) The ideal trial length for a free trial sales team

    (01:39:50) Closing thoughts

    (01:41:43) Lightning round

    Referenced:

    • Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

    • Snowflake: https://www.snowflake.com/en/

    • Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/

    • Salesforce: https://www.salesforce.com/

    • HubSpot: https://www.hubspot.com/

    • Twilio: https://www.twilio.com/

    • Cloudflare: https://www.cloudflare.com/

    • GitHub: https://github.com/

    Columbo: https://www.imdb.com/title/tt1466074/

    • What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti

    • Adobe: https://www.adobe.com/

    • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

    Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

    The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY

    • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/

    • Pipedrive: https://www.pipedrive.com/

    • Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/

    • Gong: https://www.gong.io/

    • Zendesk: https://www.zendesk.com/

    • ZoomInfo: https://www.zoominfo.com/

    • Apollo: https://www.apollo.io/

    • Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/

    • SAP: https://www.sap.com/

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • VistaPrint: https://www.vistaprint.com/

    • Procore: https://www.procore.com/

    • Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/

    • Wordpress: https://wordpress.com/

    • SaaStr University: https://app.saastruniversity.com/collections/20252

    From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691

    • Pavilion: https://www.joinpavilion.com/

    • Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw

    The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK

    Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick

    • OpusClip app: https://www.opus.pro/

    • OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/

    • SaaStr conferences: https://www.saastr.com/events/

    • Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html

    • Zoomtopia: https://zoomtopia.com/

    • Money20/20: https://us.money2020.com/

    • Shoptalk: https://shoptalk.com/

    • Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/

    • Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    🔑 Key Takeaways

    • Focus on understanding customer needs, providing valuable solutions, and building strong relationships based on trust and value, rather than pushing a sale.
    • Assess your business honestly, adapt to customer needs, and don't shy away from sales strategies that may initially seem challenging for the long-term success of your business.
    • As a founder, utilize your unique ability to connect with customers during the sales process by focusing on building relationships, asking for next steps, and closing deals confidently.
    • Focus on hiring sales reps who deeply understand and believe in your product, prioritize spending time in sales and recruiting, and trust your gut when selecting individuals passionate about your product.
    • Take the time to hire successful reps before a VP of Sales to establish a strong foundation and avoid failure in navigating early challenges.
    • Ensure your sales team, especially the VP of sales, are product experts to drive success in selling your product to your target audience.
    • Hire experienced sales reps before bringing in a VP of sales, ensure they are mature and trustworthy, and find a passionate VP willing to carry a quota for a successful sales team.
    • When hiring sales or product leaders, prioritize candidates who prioritize customer interactions, as this can lead to stronger relationships and better results for the business.
    • Hiring sales reps who can effectively engage with customers and prioritize human connections over relying solely on processes is crucial for driving business growth.
    • Sales is about solving problems and guiding customers towards the right solution, not just pushing a product. Sales reps must have knowledge and honesty to truly bring out a product's value.
    • Rushing through the hiring process can lead to costly mistakes. Take the time to thoroughly vet candidates to reduce turnover and create a successful work environment.
    • Test potential salespeople by having them sell your product, treat them with respect, focus on competitive compensation, and invest in their training for successful results.
    • Prioritize setting win-win scenarios and encouraging high performance to ensure sustained growth and profitability in sales teams.
    • Focus on quality leads and top sales performers to drive growth, rather than spreading resources thin with a large team.
    • Look for candidates who have experience selling more challenging products, as they are likely to have the skills and determination to succeed in a tougher selling environment.
    • Keep it simple by following the "rule of eight" to efficiently build and grow your sales team, avoiding title inflation and focusing on quality conversations over quick scaling.
    • Hire a VP of Sales who is willing to grow, develop strong managers, and focus on fostering their growth to set your sales team up for long-term success.
    • Focus on hiring specialized team members, create career paths for individual contributors, and foster collaboration between product and sales teams for long-term sales success.
    • Empowering a VP of Product with a budget to prioritize sales requests can prevent organizational burnout and bring scale and success to SaaS companies.
    • Collaboration and communication between product and sales teams are essential for success. By involving sales in decision-making and fostering open communication, organizations can achieve long-term success in B2B sales.
    • Regular meetings, structured processes, and aligning goals can prevent misunderstandings, create synergy, and drive success in cross-functional teams.
    • Balancing revenue goals with ethical boundaries and prioritizing customer trust over short-term gains is crucial for sustainable success in SaaS startups.
    • ''
    • Prioritize customer-centricity and long-term growth when choosing sales trial lengths to benefit both the customer and the company.
    • Always prioritize customer preferences, offer flexible payment options, focus on building trust, and let the voice of the customer guide your product strategy for sustainable growth.
    • Focus on customer satisfaction, invest in a free product edition, and champion the long tail of users to achieve success in product-led growth. Be the voice of the customer and lead by example.
    • Prioritize quality in product development to drive success, inspire collaboration, and exceed expectations. Challenge yourself to push boundaries and strive for excellence in everything you do.
    • Kindness and honesty are valuable traits that can lead to positive outcomes and lasting connections, even in challenging situations.
    • Kindness in leadership is not a sign of weakness, but a strength that fosters empathy, support, and long-term success in business and team dynamics.
    • Hosting events, even small ones, can turn customers into advocates and help boost brand awareness. Start small and scale up as your company grows.
    • Choose events wisely for maximum impact and success.
    • Approach communication with influential individuals purposefully, focusing on quality over quantity to maximize chances of connections and opportunities.

    📝 Podcast Summary

    Building Trust Through Consultative Sales Approach

    In SaaS sales, it's not about selling a product, it's about solving a problem for your customer. The key is to understand the customer's needs, provide valuable solutions, and build a strong relationship based on trust and value. Sales reps should focus on educating and guiding customers, rather than pushing a sale. By being consultative and offering genuine help, you can differentiate your product and create long-term relationships. Remember, it's not about selling a used car; it's about selling a Tesla Model 3 performance - a solution that meets your customer's needs and exceeds their expectations.

    Finding the right sales strategy for your business

    Honesty and self-awareness are crucial when determining whether or not your business needs a sales team. It's important to assess your product, market, and customer base to understand if a self-serve model or a sales-driven approach is the right fit. Be honest about the effort and resources required to acquire and retain customers, and don't shy away from sales if that's what your customers need. Embrace the feedback and behavior of your initial customers as it can shape the future of your business. Ultimately, success lies in adapting to the needs of your customers, even if it means embracing sales strategies that may seem daunting at first.

    Embrace your role as a "middler" in sales

    Sales may not be your favorite part of running a business, but it's essential for success. Even if you feel uneasy about sales, as a founder, you have a unique ability to connect with customers in the middle of the sales process. Customers love speaking directly with the CEO, and your expertise in the product and market is invaluable during these conversations. Embrace your role as a "middler" and focus on building relationships with prospects. Ultimately, it's not about being a sales expert, but about confidently asking for the next steps and closing deals. Don't underestimate the power of your middle sales skills in driving business growth.

    Hiring Sales Reps Who Believe in Your Product

    As a founder, when it comes to hiring sales reps, focus on finding individuals who deeply understand and believe in your product rather than just looking at their previous experience or company logos on their resume. The first few sales hires should be individuals you would personally buy from because they can effectively communicate your product's value to potential customers. Prioritize spending 20% of your time in sales and recruiting to ensure your calendar doesn't suffer, and look for pirates and romantics who are passionate about your product rather than individuals with massive sales operation teams. Trust your gut and prioritize hiring sales reps who truly connect with your product.

    The Importance of Hiring the Right Salesperson in Early Stages

    In the early stages, leads are precious, and hiring the right salesperson is critical. It's important to find someone who truly believes in your product and can effectively communicate its value to potential customers. Rather than rushing to hire a VP of Sales, focus on hiring two successful reps first, who can hit quota and close deals consistently. They will help establish a working sales script and identify any necessary product improvements. Rushing to hire a VP of Sales before this stage can often lead to failure, as they are not equipped to navigate the early challenges of finding product-market fit.

    Building a Knowledgeable Sales Team for Startup Success

    The early sales team needs to be product gurus for your product audience. They must be experts in the product to effectively sell it. Hiring a VP of sales who understands the product and is involved in deals is crucial for success. It's not enough for them to just be managers; they need to be actively engaged in the sales process. Avoid the mistake of hiring a VP of sales who lacks understanding of the product, as this can lead to a decrease in new bookings. Stay focused on finding salespeople who are knowledgeable about the product to drive success in your startup.

    Building a Strong Sales Team

    Before hiring a VP of sales, founders should hire two experienced sales reps who love the craft of selling and are mature enough to handle leads on their own. These reps should have a couple years of experience, ideally with deal sizes similar to the company's, and founders should trust them to handle customers without constant supervision. Additionally, founders should ensure that the VP of sales they hire is passionate about sales and willing to carry a quota, as this indicates a true dedication to the craft. By following these steps and creating a strong sales team, founders can set themselves up for success in scaling their sales efforts effectively.

    Prioritizing Customer Interaction in Leadership Roles

    When hiring sales or product leaders, it's crucial to ensure they are still passionate about engaging with customers. The best candidates are those who prioritize customer interactions over internal processes or territory planning. Whether it's a VP of sales or a chief product officer, their eagerness to meet customers within the first few weeks on the job is a strong indicator of their commitment to driving success. In today's evolving sales landscape, the ability and willingness to engage with customers directly is more important than ever. Hiring leaders who prioritize customer interactions can lead to stronger relationships and ultimately drive better results for the business.

    Building Genuine Customer Relationships for Business Growth

    Customer success roles require a genuine willingness to engage and connect with customers. Hiring burnt-out veterans who avoid customer interactions can be detrimental to a company's growth. Even at larger revenue levels, leaders like Marc Benioff still prioritize meeting customers face-to-face. When hiring early sales reps, look for those who can effectively sell the product in a simple and convincing manner. Avoid falling into the trap of relying solely on processes without genuine customer interactions, as human connections play a vital role in building successful customer relationships and driving business growth.

    Understanding and Selling Products Effectively

    Sales reps need to put in the effort to truly understand and sell their product. Whether it's watching explainer videos, attending webinars, or simply knowing the core problem the product solves, this knowledge is crucial. Sales is about solving problems, not just pushing a product. The best reps are honest, confident, and willing to guide potential customers towards the right solution, even if it means saying no for now. Software can be magical when done right, but it still requires effort from sales reps to truly bring out its value. Sales is not about tricks or tactics; it's about genuinely helping customers.

    Prioritize quality over speed in hiring

    Hiring processes should not skip essential steps like reference checks and pitching exercises. Rushing to fill roles without thoroughly vetting candidates can lead to costly mistakes for both the company and the hire. It's crucial to take the time to ensure each hire is the right fit and fully understands the responsibilities of the role. By prioritizing quality over speed in the hiring process, founders and recruiters can reduce turnover rates and create a more successful and harmonious work environment for all parties involved. Remember, taking shortcuts in hiring can ultimately result in avoidable problems down the road.

    Screening and Training Salespersons Effectively

    Before hiring a salesperson, have them sell your product for real. Allow them to do a demo and take their time if needed. Treat them with respect and give them the opportunity to showcase their selling abilities. If a candidate refuses to do a demo, they may not be the right fit for the role. When it comes to compensation and quota, focus on ensuring that the sales rep can close more than they take home in the early stages. Paying market rates is crucial, even if it may seem daunting at first. Invest in your sales team to see if the experiment will yield positive results.

    Creating Effective Sales Compensation Plans

    When structuring sales compensation plans, it's crucial to focus on practicality and long-term success. Key points include setting win-win scenarios, aiming for sales reps to bring in four to five times what they take home, and adjusting expectations over time. It's essential to prioritize sales reps being accretive and closing deals effectively rather than solely focusing on numbers and acronyms like OTE. By creating a plan where sales reps can exceed their take-home pay through their performance, businesses can ensure sustained growth and success. Remember, it's better to have fewer, high-performing reps than many underperforming ones to avoid burning cash and maintain profitability.

    Strategic capacity planning for sales success

    Capacity planning and focusing on quality over quantity is crucial for a company's growth and success. It's important to concentrate your leads with your best closers in the early days, rather than spreading resources thin with a large team. Supporting and guiding sales reps is necessary, but mishires can be detrimental to both the company and the individual. Sales success can vary drastically depending on the environment, so identifying a good fit early on is key. Remember, it's better to have a small team of top performers making a lot of money than a large team struggling to meet targets.

    Hiring Successful Sales Reps

    When hiring sales reps, it is crucial to look for candidates whose last product was harder to sell than yours. This indicates that they have the skills and determination to tackle challenges and succeed in a tougher selling environment. Hiring someone who found their previous product easier to sell may not have the necessary skills to effectively sell your product. Look for candidates who have experience in a more competitive market or a more technical product, as they are likely to excel in selling your offering. By carefully considering the difficulty of their previous sales experience, you can set your sales team up for success.

    The Rule of Eight in Sales Organization Scaling

    Simplicity is key in scaling a sales organization. By following the "rule of eight" where eight SDRs need one manager, eight AEs need a director, and so on, you can efficiently build and grow your sales team. Avoiding title inflation and understanding that most first heads of sales should be a stretch VP of Sales can help ensure that your team is set up for success. Focus on having fewer SDRs who can have better conversations rather than trying to scale too quickly. By keeping it simple and following these guidelines, you can effectively structure and grow your sales organization.

    Hiring a VP of Sales for Success

    When hiring your first VP of Sales, aim for a stretch candidate who is willing to grow and evolve in the role. It is crucial for their career development, personal growth, and the success of the equity. Additionally, ensure that your VP of Sales can effectively hire and develop strong managers underneath them. Without a solid leadership team, the organization may struggle to scale and reach its full potential. By focusing on hiring the right people and fostering their growth, you can set your sales team up for long-term success and prevent cracks in the organization's foundation.

    Specialization and Collaboration: Keys to a Successful Sales Team

    Specialization is key in building a successful sales team. While the idea of a full-stack account executive may sound appealing, the reality is that most AEs thrive when focused on closing deals and working leads. Hiring specialized team members, such as SDRs to generate demand, can help create a more effective sales process. Additionally, founders should not expect sales executives to naturally transition into management roles. Instead, creating a career path for top-performing individual contributors can lead to long-term success. Collaboration between product and sales teams is also crucial, with product managers being deeply involved in sales to ensure alignment and success in meeting customer needs.

    The Strategic Power of a VP of Product in B2B Companies

    Having a strong VP of Product can be a game-changer in B2B companies. The VP of Product acts like a mini CEO in big customer meetings, making commitments and owning the roadmap. They have the ability to connect different pieces of the product that don't naturally align and have the gravitas to work with large customers. By empowering the VP of Product with a budget each quarter to prioritize sales requests, it can prevent the tail from wagging the dog and burning out the organization. This strategic weapon of a VP of Product can bring scale and success to SaaS companies when utilized effectively.

    Building a Strong Relationship Between Product and Sales Teams

    Collaboration and communication between product and sales teams are crucial for success. Product leaders should provide a clear budget and roadmap to sales, allowing for input and adjustments within reason. By involving sales in the decision-making process and actively listening to their needs, teams can work together effectively to balance priorities and make informed decisions. It's normal to experience some tension between product and sales, but it's a sign of a thriving organization. By fostering a culture of open communication and mutual respect, companies can prevent breakdowns and achieve long-term success in B2B sales.

    Effective communication and alignment in cross-functional teams

    Communication and alignment are crucial in cross-functional teams. Pushing decisions up to the appropriate leaders and ensuring regular meetings where sales and product teams share priorities can prevent misunderstandings and create synergy. It's essential to have structured processes in place to avoid tension and facilitate productive discussions. Additionally, aligning KPIs and OKRs with overall revenue goals can be beneficial, but it's important to balance financial incentives with customer satisfaction. Learning from industry trends and experiences can help in making informed decisions to drive success and avoid potentially damaging outcomes like strained customer relationships due to misplaced focus on revenue metrics.

    Ensuring Ethical Revenue Growth in Startups

    Weaponizing customer success or product teams may lead to short-term gains but at the cost of long-term customer satisfaction and product integrity. It's crucial for founders to align product teams with revenue goals without crossing ethical boundaries. Allowing room for experimentation and failure, within limits, fosters innovation and growth in startups. Avoiding the pressure to prioritize revenue over customer experience can prevent dark practices that may yield quick wins but damage brand reputation in the long run. Balancing revenue generation with maintaining customer trust is key to sustainable success in SaaS companies.

    ''

    In order to build a successful B2B company and reach billion dollar revenue numbers, founders must focus on the power of compounding and reducing churn. By relentlessly working to bring down churn rates and always having a next step in sales meetings, founders can steadily move the ball down the field and ultimately secure the deals needed to grow their business. It's not just about asking for money, but about continuously progressing towards the next milestone. By understanding the importance of compounding revenue and focusing on customer retention, startups can position themselves for long-term success and achieve billion dollar status in the future.

    Navigating the Sales Skill Landscape

    When it comes to improving sales skills, there are valuable resources like SaaStr.University and the book "From Impossible To Inevitable" that can offer insights and tips. It's important to be cautious of the abundance of sales courses available online and to prioritize customer-centricity when choosing trial lengths. While some companies benefit from shorter trials to close deals quickly, others, like Slack and Zoom, have found success with infinite trials. Ultimately, founders and product teams should make decisions that benefit both the customer and the company's long-term growth, rather than following short-term trends or advice from those outside the industry.

    Prioritizing Customer Needs for Business Success

    It's essential to prioritize customer needs and preferences in your business decisions. Instead of forcing customers into annual contracts, consider offering flexible payment options like monthly subscriptions to align with their preferences. Focus on building trust and long-term relationships by providing value that justifies price increases and extending free trials to truly showcase the benefits of your product. Remember, the voice of the customer should guide your product strategy, not just sales or marketing tactics. By putting the customer first and earning their loyalty, you can create a sustainable business that grows to $1 billion ARR organically.

    Prioritizing Customer Satisfaction for Product-Led Growth

    Focusing on delivering more value than you take out for your customers, investing in a free edition of your product, and championing the long tail of users can lead to success in product-led growth. While it may be tempting to prioritize monetization, nurturing the broader audience and making customers happy should be the top priority. As a product leader, be the voice of the customer, work harder to find delight in making customers happy, and be the vanguard in your company. This year, make it the year of the customer and strive to do great things in the world of product development.

    Building Excellence Through Product Innovation

    Focus on delivering great products can energize your team and drive success. Even if you're unsure of the exact strategy for getting more leads or achieving growth, investing in the quality of the code you write and the products you ship can make a significant impact. Challenge yourself and your team to ship three great things this year. Inspire collaboration across departments by prioritizing excellence in product development. Like a well-executed movie or TV show, exceptional software delights users and exceeds expectations. Be the Maverick in your industry, pushing boundaries and striving for excellence in everything you do.

    The Power of Kindness in Business and Life

    Being kind is crucial in both work and life. Jason Lemkin reflects on the importance of showing kindness even in challenging situations. He emphasizes that while he may not always be nice, he values honesty and kindness above all. Lemkin shares a personal experience where he regrets not being kind to a customer who switched to a competitor. This serves as a reminder that kindness can make a significant impact on relationships and outcomes. In a world where success often comes at the expense of others, choosing to be kind can lead to lasting connections and positive results.

    The Power of Kindness in Leadership

    Kindness is key in leadership and business. While there is pressure to be relentless and cutthroat, successful CEOs and leaders are kind, not soft. Being kind doesn't mean being weak; it means being committed, making tough decisions, and treating employees with empathy. Remember that any failure within your team ultimately falls on your shoulders, as you hired them. Strive to be kind in every interaction and challenge yourself to be empathetic and supportive. It may be a simple concept, but it can have a lasting impact on your career and team dynamics. Be kind, always.

    Building Customer Relationships Through Events

    Hosting events for your customers and prospects can be a powerful marketing tool, even if it starts small with meetups or steak dinners. By bringing your customers together, they can become your best advocates and help sell your product or service to prospects. Start small and inexpensive, gradually scaling up as your company grows and revenue allows. While large scale events can be incredibly expensive, they can also be incredibly impactful in terms of brand awareness and community building. Remember, your customers are key to your success, and creating opportunities for them to connect can yield significant returns in the long run.

    Strategic Event Planning for Success

    Hosting events can be a risky and expensive venture, with potential for significant financial loss. However, when done strategically and at scale, events can be extremely profitable and valuable for building community and networking. It's essential to carefully choose which events to attend or host, focusing on those that attract the best attendees and offer meaningful opportunities for engagement. While smaller meetups may have their place, larger, well-planned events can bring together top industry leaders and provide a valuable platform for marketing and networking. Ultimately, the key is to be selective and strategic in your event participation to maximize the benefits and minimize the risks.

    Crafting Compelling Messages for Strategic Communication

    Strategic communication through email and social media can be a powerful tool to reach influential individuals in any industry. Jason Lemkin emphasizes the importance of crafting compelling messages that stand out and maximize the chances of getting read and potentially receiving a response. While it may be challenging to secure an hour of someone's time, reaching out with concise and thoughtful inquiries can lead to valuable connections and opportunities. Remember, quality over quantity is key when it comes to engaging with key figures, so approach each interaction with a clear purpose and strategic mindset for the best chance of success.

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    Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast)

    Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast)

    Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss:

    • How Nubank builds a fanatical user base

    • Tactics for driving word-of-mouth growth

    • Measuring customer love through the Sean Ellis score

    • The importance of strategic clarity

    • The role of category design in creating successful products

    • Why companies should strive to be “fundamentally different,” not “incrementally better”

    • Nubank’s vision for an AI-powered banking future

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal

    Where to find Jag Duggal:

    • LinkedIn: https://www.linkedin.com/in/jagduggal/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Jag’s background

    (04:34) Nubank’s remarkable achievements

    (06:01) Nubank’s product development process

    (11:23) Nubank’s values

    (12:16) Building products people love fanatically

    (15:21) The Sean Ellis score

    (21:27) An example project using the Sean Ellis score

    (25:07) Picking up the phone and calling customers

    (28:20) The importance of starting small and iterating

    (30:42) Pushing back effectively

    (34:10) Uncovering pain points through customer research

    (37:53) An example of setting a clear hypothesis

    (42:01) Developing a strategy

    (52:16) “Be fundamentally different, not incrementally better”

    (53:10) Category design

    (57:37) Nubank’s founding story and goals for the future

    (01:00:46) Advice for adding new product lines

    (01:03:46) The future of fintech and banking

    (01:09:23) AI corner

    (01:12:34) Failure corner

    (01:20:24) Key takeaways

    (01:22:11) Lightning round

    Referenced:

    • Nubank: https://nubank.com.br/en/

    • Coinbase: https://www.coinbase.com/

    • Robinhood: https://www.robinhood.com/

    • SoFi: https://www.sofi.com/

    • Affirm: https://www.affirm.com/

    • Lemonade: https://www.lemfi.com/

    • Bank of America: https://www.bankofamerica.com/

    • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao

    • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea

    • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875

    • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira

    • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible

    • Sequoia Capital: https://www.sequoiacap.com/

    • Churrascaria: https://en.wikipedia.org/wiki/Churrascaria

    • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/

    • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/

    • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

    • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

    • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

    • Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/

    • Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY

    • The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness

    • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

    • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

    Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

    The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

    • How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher

    Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619

    Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • Citi: https://www.citi.com/

    • Santander Bank: https://www.santanderbank.com/

    • Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

    • Harvard Kennedy School: https://www.hks.harvard.edu/

    • Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/

    • Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg

    • Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html

    • Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272

    From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/

    The Gilded Age on HBO: https://www.hbo.com/the-gilded-age

    • Lomi: https://lomi.com/

    • Nubank careers: https://international.nubank.com.br/careers/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    A framework for PM skill development | Vikrama Dhiman (Gojek)

    A framework for PM skill development | Vikrama Dhiman (Gojek)

    Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss:

    • The most common traits among successful product managers

    • The 3 W’s framework for PM career growth

    • The Four A’s of leveling up in product management

    • The right way to push back as a PM

    • Common pitfalls that stall PM careers

    • Vikrama’s advice for transitioning into product management

    • Why intent alone is not enough

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development

    Where to find Vikrama Dhiman:

    • X: https://twitter.com/vikramadhiman

    • LinkedIn: https://www.linkedin.com/in/vikrama/

    • Website: https://www.vikramadhiman.com/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Vikrama’s background

    (03:56) Three common traits among great PMs

    (07:09) The first W: What you produce

    (15:40) The second W: What you bring to the table

    (18:58) The third W: What’s your operating model?

    (20:36) Three traits that make you a great PM to work with

    (21:49) How to improve the quality and quantity of your outputs

    (23:26) The art of the pushback

    (26:55) Common factors that impede career growth

    (33:39) Vikrama’s personal reflections

    (39:33) Choosing which skill(s) to focus on developing

    (46:28) The ambiguity of the PM role

    (51:47) The 8 axis for PM growth

    (56:57) Contrarian corner: Why intent alone is not enough

    (59:30) Lightning round

    Referenced:

    • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom

    • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock

    • Gojek: https://www.gojek.com/en-id

    • SQL: https://en.wikipedia.org/wiki/SQL

    • Oracle: https://www.oracle.com/

    • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja

    • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id

    • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup

    • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your

    • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/

    • Workday: https://www.workday.com/

    • Salesforce: https://www.salesforce.com/

    Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681

    Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X

    Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

    Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK

    Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F

    • DramaBox: https://www.dramaboxapp.com/

    Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/

    Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF

    • 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Business strategy with Hamilton Helmer (author of 7 Powers)

    Business strategy with Hamilton Helmer (author of 7 Powers)

    Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss:

    • Potential sources of power that startups should develop from an early stage

    • Common misconceptions among companies about the types of power they possess

    • How power relates to strategy

    • The difference between a moat and a power

    • Practical strategies for non-leaders to leverage insights about power and strategy in their work

    • AI’s impact on competitive advantages and barriers to entry

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    Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer

    Where to find Hamilton Helmer:

    • X: https://twitter.com/hamiltonhelmer

    • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/

    • Website: https://7powers.com/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Hamilton’s background

    (04:08) When power becomes important

    (08:24) How strategy relates to power

    (12:09) How power informs strategy

    (14:46) The sequence of powers

    (21:13) Common misconceptions

    (24:39) Network effects vs. network economies

    (26:58) Uber’s success

    (29:16) Moats vs. powers

    (31:12) Strategies for non-leaders to leverage power and strategy

    (37:51) Advice on how to become a strategic thinker

    (39:27) AI’s impact on the seven powers

    (45:43) Why moving fast is not a power

    (50:24) Three things that create value in a company

    (51:16) The debt trajectory of the U.S.

    (56:35) Optimism for the future

    (59:25) Lightning round

    Referenced:

    7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319

    • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann

    • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor

    • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/

    • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors

    • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/

    • Strategy Capital: https://strategycapital.com/

    • Warren Buffett: https://www.forbes.com/profile/warren-buffett/

    • Charlie Munger: https://www.forbes.com/profile/charles-munger/

    • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack

    • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6

    •  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973

    • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html

    • Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/

    • What Is Strategy?: https://hbr.org/1996/11/what-is-strategy

    • TSMC: https://www.tsmc.com/english

    • Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System

    • America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/

    • Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke

    • Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes

    • Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter

    Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982

    The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311

    The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X

    American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX

    • Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/

    • Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland

    • Ogilvy: https://www.ogilvy.com/

    • Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005

    • Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill

    Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498

    The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)

    • Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit”, former pro poker player)

    This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit”, former pro poker player)

    Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover:

    • What Annie learned from the late Daniel Kahneman

    • The power of pre-mortems and “kill criteria”

    • The relationship between money and happiness

    • The power of “mental time travel”

    • The nominal group technique for better decision quality

    • How First Round Capital improved their decision-making process

    • Many tactical decision-making frameworks

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    Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

    Where to find Annie Duke:

    • X: https://twitter.com/AnnieDuke

    • LinkedIn: https://www.linkedin.com/in/annie-duke/

    • Website: https://www.annieduke.com/

    • Substack: https://www.annieduke.com/substack/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Annie’s background

    (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness

    (09:15) The importance of unconditional love in parenting

    (15:15) Mental time travel and “nevertheless”

    (20:06) The extent of improvement possible in decision-making 

    (24:54) Independent brainstorming for better decisions

    (35:36) Making sure people feel heard

    (42:41) The “3Ds” framework to make better decisions

    (44:49) Decision quality

    (55:46) Improving decision-making at First Round Capital

    (01:05:05) Using pre-mortems and kill criteria

    (01:10:15) Making explicit what’s implicit

    (01:10:55) The challenges of quitting and knowing when to walk away

    (01:19:23) Where to find Annie

    Referenced:

    • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html

    • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration

    • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research#

    • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/

    • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut

    • Cass Sunstein on X: https://twitter.com/CassSunstein

    • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside

    • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    • First Round Capital: https://firstround.com/

    • Brett Berson on X: https://twitter.com/brettberson

    • Renegade Partners: https://www.renegadepartners.com/

    • Renata Quintini on X: https://twitter.com/rquintini

    • Roseanne Wincek on X: https://twitter.com/imthemusic

    • Josh Kopelman on X: https://twitter.com/joshk

    • Bill Trenchard on X: https://twitter.com/btrenchard

    • Linnea Gandhi on X: https://twitter.com/linneagandhi

    • Maurice Schweitzer on X: https://twitter.com/me_schweitzer

    • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf

    • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/

    Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/

    • Richard Thaler on X: https://twitter.com/R_Thaler

    • Stewart Butterfield on X: https://twitter.com/stewart

    • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

    • How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66

    • The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/

    • The Alliance for Decision Education: https://alliancefordecisioneducation.org/

    • Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour

    Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour

    Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss:

    • The story of being let go from Twitter after Elon’s acquisition

    • How he turned Twitter’s stagnant culture around

    • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done

    • Why Periscope failed

    • Advice for building consumer products

    • When to copy, when to innovate

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    Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour

    Where to find Kayvon Beykpour:

    • X: https://twitter.com/kayvz

    • LinkedIn: https://www.linkedin.com/in/kayvz/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Kayvon’s background

    (04:31) Getting Elon up to speed at Twitter

    (11:34) The story of being let go from Twitter after Elon’s acquisition

    (21:09) Changing the product culture at Twitter

    (29:44) Building the “hide replies” feature

    (32:02) Sacred crows, taking bold bets, and reigniting growth

    (34:28) Aquihires and their impact

    (42:40) Tips for successful acquisitions and staffing

    (47:00) The limitations of frameworks like JTBD

    (53:20) Signs you’ve gone too far with a framework

    (57:44) Lessons from building Periscope

    (01:00:41) Reasons why Periscope failed

    (01:07:24) The challenges of implementing video at Twitter

    (01:12:05) Copying ideas in good taste

    (01:17:58) How to get better at building consumer products

    (01:19:51) What Kayvon is building

    (01:20:31) Lightning round

    Referenced:

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3

    • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/

    • Elon Musk on X: https://twitter.com/elonmusk

    • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/

    • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/

    • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc.

    • Keith Coleman on X: https://twitter.com/kcoleman

    • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/

    • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html

    • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/

    • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

    • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/

    • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/

    • Chris Sacca’s website: https://chrissacca.com/

    • Facebook Live: https://www.facebook.com/formedia/tools/facebook-live

    • Kevin Hart on X: https://twitter.com/KevinHart4real

    • Clubhouse: https://www.clubhouse.com/

    • Vine: https://en.wikipedia.org/wiki/Vine_(service)

    • Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/

    • Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/

    Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624

    Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW

    The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM

    Star Trek official site: https://www.startrek.com/

    Dune: part 2: https://www.dunemovie.com/

    Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer

    • Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942

    Devs on Hulu: https://www.fxnetworks.com/shows/devs

    • Nick Offerman on X: https://twitter.com/nick_offerman

    3 Body Problem on Netflix: https://www.netflix.com/title/81024821

    • Perplexity AI: https://www.perplexity.ai/

    • Particle: https://www.particle.news/

    • Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”)

    How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”)

    Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss:

    • The benefits of building robust relationships, in life and work

    • The 15% rule, and how it will help you build better relationships

    • The power of vulnerability

    • Examples of how to practice vulnerability

    • Why mental models you build early in life hold you back later

    • The “three realities” and “the net”

    • The art of inquiry

    • Practical tips for avoiding defensiveness when getting feedback

    • The impact of long Covid on Carole’s life

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

    Where to find Carole Robin:

    • LinkedIn: https://www.linkedin.com/in/carole-robin/

    • Email: carolerobinllc@gmail.com

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Carole’s background

    (05:17) The importance of building robust relationships

    (10:20) The “Touchy Feely” course at Stanford

    (13:29) An example of the in-class experience

    (17:19) Leaders in Tech: developing interpersonal competence

    (21:36) Progressive disclosure and the 15% rule

    (24:28) Appropriate disclosure

    (26:52) The power of vulnerability

    (34:57) Admitting mistakes and sharing feelings

    (37:08) Understanding mental models

    (42:57) The “three realities” framework

    (53:52) The power of feedback and personal change

    (58:47) The art of inquiry

    (01:03:27) How to get better at giving feedback

    (01:07:47) Exercises and continued learning

    (01:10:49) “Advice hinders relationships”

    (01:16:49) Failure corner: AFOG

    (01:20:30) Takeaways

    (01:21:51) Lessons from long Covid

    Referenced:

    • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships

    Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ

    • Leaders in Tech: https://leadersintech.org/

    • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows

    • Steve Jobs: https://www.forbes.com/profile/steve-jobs/

    • Sheryl Sandberg on X: https://twitter.com/sherylsandberg

    • Ursula Burns: https://www.forbes.com/profile/ursula-burns/

    • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications

    • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html

    • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable

    • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/

    • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/

    • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://pen-name.notion.site/Carole-Robin-4-25-5d47d38a620e4636966d31f4bf3c7d00?pvs=4

    Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

    • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

    • Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2

    • Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma)

    Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma)

    Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss:

    • How to effectively take ideas from 0 to 1 at larger companies

    • How to craft a compelling vision

    • The importance of vulnerability and feedback

    • The role of intuition and product sense in making decisions

    • How to practically communicate your vision

    • How to balance collaboration and strong opinions

    • Advice for building a strong team culture

    • Pivoting with grace and enthusiasm

    • The current AI revolution and its impact on PM

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

    Where to find Mihika Kapoor:

    • X: https://twitter.com/mihikapoor

    • LinkedIn: https://www.linkedin.com/in/mihikakapoor/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Mihika’s background

    (04:29) Core attributes of great product managers

    (07:34) Crafting a compelling vision

    (12:12) The vision behind FigJam 

    (18:25) Delivering a vision without design or engineering skills

    (21:52) Creating momentum

    (26:36) The importance of strong conviction

    (27:45) Direct communication

    (32:48) Building hype

    (42:20) Immersing yourself in user insights

    (47:16) Operationalizing user insights  

    (50:33) Caring deeply about what you build

    (54:01) Finding passion in your work

    (57:00) Building a strong culture

    (01:07:07) Pivoting with grace and enthusiasm

    (01:11:48) Design Nation

    (01:13:15) Mihika’s weaknesses

    (01:16:07) Building new products at larger companies

    (01:20:50) Coming up with a great idea

    (01:22:49) The key to going from 0 to 1

    (01:26:47) Spreading the idea across the company

    (01:29:15) Closing thoughts

    (01:32:11) Lightning round

    Referenced:

    • Figma: https://www.figma.com/

    • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/

    The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949

    • FigJam: https://www.figma.com/figjam/

    • Cognition: https://www.cognition-labs.com/

    • Devin: https://www.cognition-labs.com/introducing-devin

    • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/

    • Replit: https://replit.com/

    • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/

    • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/

    • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625

    • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/

    • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/

    • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/

    • Config: https://config.figma.com/

    • Dev Mode: https://www.figma.com/dev-mode/

    • Asana: https://asana.com/

    • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/

    • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free

    • Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

    • Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/

    Design Disruptors: https://www.invisionapp.com/films/design-disruptors

    • Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/

    • Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/

    • Design Nation: https://dn.businesstoday.org/

    • Stuart Weitzman on X: https://twitter.com/StuartWeitzman

    • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

    • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/

    • Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot

    • Hestia: https://en.wikipedia.org/wiki/Hestia

    Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076

    Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/

    Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

    The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

    Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

    Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

    Dune: Part 2: https://www.dunemovie.com/

    • Arc browser: https://arc.net/

    • Pika: https://pika.art/home

    • The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)

    Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)

    Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

    • Why founders need to adopt the mindset “Just don’t die”

    • The most common reason startups fail

    • When to pivot, and characteristics of a good pivot

    • The concept of “tar pit ideas” and examples of bad startup ideas

    • Why investors say no to startups

    • The importance of market size in investment decisions

    • The pitfalls of founders over-delegating

    • Effective ways to talk to customers

    • 20 ideas Dalton is looking to fund

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

    Where to find Dalton Caldwell:

    • X: https://twitter.com/daltonc

    • LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Dalton’s background

    (04:41) The value of simple advice

    (07:04) Dalton’s advice: “Just don’t die”

    (08:39) Knowing when to stop

    (11:45) Deciding to pivot

    (14:26) Characteristics of a good pivot

    (17:53) Knowing when to pivot

    (19:03) Zip’s journey and finding a market

    (21:22) Why Dalton says to “Move towards the mountains and the desert”

    (23:45) Tar pit ideas

    (26:49) Understanding why investors say no

    (29:14) The importance of market size

    (32:16) Avoiding over-delegation and hiring senior people too early

    (36:43) Why startups fail

    (40:30) Effectively talking to customers

    (45:17) Examples of startups hustling to talk to customers

    (48:01) Patterns of successful startups

    (52:05) YC’s Request for Startups

    (55:37) Early days of Silicon Valley

    (01:05:33) Contrarian corner: growth hacking for early startups

    (01:09:28) Failure corner

    (01:11:15) Closing thoughts

    (01:12:22) Lightning round

    Referenced:

    • Y Combinator: https://www.ycombinator.com/

    • Tiger Woods’s website: https://tigerwoods.com/

    • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

    • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

    • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

    • Brex: https://www.brex.com/

    • Retool: https://retool.com/

    • Segment: https://segment.com/

    • Mixpanel: https://mixpanel.com/

    • Whatnot: https://www.whatnot.com/

    • Andreessen Horowitz: https://a16z.com/

    • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

    • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

    • Zip: https://ziphq.com/

    • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

    • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

    • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

    • Foursquare: https://foursquare.com/

    • Razorpay: https://razorpay.com/

    • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

    • Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

    • Milk Video: https://milkvideo.com/

    • Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

    • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

    • Collison installation: https://news.ycombinator.com/item?id=18400504

    • Stripe: https://stripe.com/

    • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

    • John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

    • Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

    • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

    • Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

    • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

    • YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

    • ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

    • Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

    • New space companies: https://www.ycombinator.com/rfs#new-space-companies

    • A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

    • Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

    • New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

    • Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

    • Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

    • Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

    • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

    • Sam Altman on X: https://twitter.com/sama

    • Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

    • Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

    • Marc Andreessen on X: https://twitter.com/pmarca

    • Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

    • Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

    Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

    Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

    • Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

    The Sopranos on HBO: https://www.hbo.com/the-sopranos

    The Wire on HBO: https://www.hbo.com/the-wire

    Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

    • Oura ring: https://ouraring.com/

    • Apple watch: https://www.apple.com/watch/

    • SiPhox: https://siphoxhealth.com/

    • Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

    • How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

    • The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

    The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

    David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss:

    • How GitLab operationalizes transparency

    • The philosophy behind recording and sharing team meetings on YouTube

    • Their extensive public employee handbook

    • GitLab’s core value of having “short toes”

    • Challenges and advice for doing remote work well

    • Strategies for ensuring effective communication in a remote work environment

    • GitLab’s breadth-over-depth strategy

    • The company’s unique approach to AI

    • The value of using humor in high-stakes conversations

    Brought to you by:

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    Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way

    Where to find David DeSanto:

    • X: https://twitter.com/david_desanto

    • LinkedIn: https://www.linkedin.com/in/ddesanto/

    • Threads: https://www.threads.net/@david.the.beard

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) David’s background

    (04:20) Maintaining an epic beard

    (05:29) Why GitLab publicly shares team meetings

    (09:49) The GitLab Handbook

    (11:30) GitLab’s issue tracker

    (14:29) How to successfully build a culture of transparency

    (18:11) Benefits of operating with transparency

    (19:55) The value of building in public

    (21:53) How GitLab implements their core value of kindness

    (25:16) What it means to have “short toes”

    (27:41) Other core values

    (32:16) Common reasons for not fitting in at GitLab

    (34:42) Advice for remote teams

    (42:04) Advice for getting into product

    (43:52) Advice for PMs who are struggling in a remote world

    (48:25) Specific tools that help with remote work

    (53:13) Time zones and remote work

    (57:18) Breadth-over-depth strategy

    (01:04:14) AI at GitLab

    (01:13:11) GitLab’s products and solutions

    (01:14:54) Lightning round

    Referenced:

    • GitLab: https://about.gitlab.com/

    • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4

    • The GitLab Handbook: https://handbook.gitlab.com/

    • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/

    • Y Combinator: https://www.ycombinator.com/

    • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/

    • Salesforce: https://www.salesforce.com/

    • GitLab values: https://handbook.gitlab.com/handbook/values

    • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure

    • GitLab direction: https://about.gitlab.com/direction/

    • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7

    • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg

    • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

    • HubSpot: https://www.hubspot.com/

    Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

    • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/

    • Open-core model: https://en.wikipedia.org/wiki/Open-core_model

    • GitLab Duo: https://about.gitlab.com/gitlab-duo/

    • GitLab Docs: https://docs.gitlab.com/

    • Anthropic: https://www.anthropic.com/

    • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/

    Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

    • The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/

    The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3

    Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416

    • Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B

    • The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/

    • Artifact News: https://artifact.news/

    • Superhuman: https://superhuman.com/

    • Arc browser: https://arc.net/

    • An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

    A framework for finding product-market fit | Todd Jackson (First Round Capital)

    A framework for finding product-market fit | Todd Jackson (First Round Capital)

    Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss:

    • Why product-market fit (PMF) matters

    • First Round Capital’s four-part PMF framework

    • Level one: Nascent product-market fit

    • Level two: Developing product-market fit

    • Level three: Strong product-market fit

    • Level four: Extreme product-market fit

    • Examples of companies at each level

    • How to know if you’re stuck at a level, and how to get unstuck

    • What to change if you’re stuck: persona, problem, promise, and product

    • The goals and challenges at each stage

    Brought to you by:

    WorkOS—The modern API for auth and user identity

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    Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market

    Where to find Todd Jackson:

    • X: https://twitter.com/tjack

    • LinkedIn: https://www.linkedin.com/in/toddj0/

    Where to find Lenny:

    • Newsletter: https://www.lennysnewsletter.com

    • X: https://twitter.com/lennysan

    • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

    In this episode, we cover:

    (00:00) Todd’s background

    (06:07) First Round Capital’s PMF framework

    (09:07) Why product-market fit is so important

    (11:02) Who can benefit from this framework

    (12:55) The product-market fit method

    (16:54) Broad overview of the framework

    (21:35) Level one: nascent product-market fit

    (33:16) The four P’s

    (39:13) Level two: developing product-market fit

    (49:13) Signs you’re stuck at level two, and what to do

    (55:12) Level three: strong product-market fit

    (01:00:17) Signs you’re stuck at level three, and what to do

    (01:02:22) Level four: extreme product-market fit

    (01:06:55) Rough timelines for each level

    (01:11:18) A quick recap of the framework

    (01:12:15) Diving deeper on the four P’s: what to do if you’re stuck

    (01:13:56) Dollar-driven discovery

    (01:25:11) Apply for the product-market-fit method program

    Referenced:

    • First Round: https://firstround.com/

    • Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup

    • Dropbox: https://www.dropbox.com/

    • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/

    • How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

    • How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea

    • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

    • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket

    • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

    • Product-market fit method: http://pmf.firstround.com/

    • Stripe: https://stripe.com/

    • Plaid: https://plaid.com/

    • Paths to PMF: https://review.firstround.com/series/product-market-fit/

    • WeWork: https://www.wework.com/

    • Casper: https://casper.com/

    • Vanta: https://www.vanta.com/

    • Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

    • Ramp: https://ramp.com/

    • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/

    • Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/

    • Lattice: https://lattice.com/

    • Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/

    • Positioning: https://www.lennysnewsletter.com/p/positioning

    • Retool: https://retool.com/

    • David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/

    • Persona: https://withpersona.com/

    • Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/

    • Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/

    • Looker: https://en.wikipedia.org/wiki/Looker_(company)

    • Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/

    • Ironclad: https://ironcladapp.com/

    • Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ

    • Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/

    • Verkada: https://www.verkada.com/

    • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/

    • Databricks: https://www.databricks.com/

    • Stripe Radar: https://stripe.com/radar

    • Stripe Atlas: https://stripe.com/atlas

    • Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader

    • Cash App: https://cash.app/

    • Square Checking: https://squareup.com/us/en/campaign/banking/checking

    • Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital

    • Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/

    • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

    • Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/

    • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/

    • Simon Kucher: https://www.simon-kucher.com/

    Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

    Lenny may be an investor in the companies discussed.



    Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe