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    Lessons Learned from Investing in 22 Companies (Pt.1) | Ep 608

    enSeptember 19, 2023

    Podcast Summary

    • Lessons from growing 22 profitable companiesUnderstand audience, build a brand through giving, and work with a select few high-potential companies to generate proprietary deal flow

      Entrepreneurship requires a broad understanding of various aspects of a business, allowing one to identify and address macro-level constraints. The speaker, who aims to build a billion-dollar business, shares lessons from investing in and growing 22 profitable companies over the last 3 years. He emphasizes the importance of understanding the audience and building a brand through giving, rather than trying to sell to everyone. The speaker's strategy is to work with a select few high-potential companies, and he shares that his business, Acquisition.com, receives 2,000 applications per month but only works with US and Canada-based companies with a minimum of $1,000,000 in profit. The speaker's theory combines old investing methods with new social media strategies to generate proprietary deal flow. This approach allows him to build a strong brand and work with a select few promising companies.

    • Invest in quality over quantityFocus on a few high-quality companies for better outcomes, rather than spreading investments thinly across many.

      Successful investing is not about quantity but quality. The speaker emphasizes that it's better to invest in a few high-quality companies rather than many. They share their experience of having fewer deals but higher quality businesses in their portfolio, which has led to better outcomes. The speaker also explains that their approach is active, meaning they are deeply involved in the companies they invest in and work to grow them. They have a large team dedicated to this effort. This active approach allows them to identify the right businesses and guide their growth, leading to a steady investing cadence.

    • Investor focuses on significant investments with substantial ownership stakeThis investor aims for active involvement, substantial ownership, and creating value for all parties in companies undergoing growth from smaller to larger profit margins, where greatest enterprise value is unlocked.

      This investor focuses on making significant investments in businesses where they can actively contribute resources, and in return, they aim for a substantial ownership stake. The investor's goal is to grow the business and create value for all parties involved, aiming to make every deal the best one in the investor's counterpart's life. The investor's strategy is to target companies in various industries undergoing growth from smaller to larger profit margins, as this is where the greatest enterprise value is unlocked. The investor also mentioned that the median transaction for small businesses is typically lower than publicly traded companies' valuations, and the greatest value is often created in the jump from smaller to larger profit margins.

    • Growing companies for enterprise valueIdentify businesses with $1M+ EBITDA or $2M+ profit, product-market fit, growth, and cash flow for successful investing, focusing on scaling established businesses instead of trial and error.

      Successful investing involves growing companies independently of the investor's influence to build enterprise value, rather than becoming tied to a company's success and relying on it for employment. The investor shared statistics of increasing top line and profit by significant multiples within the first 12 and 24 months. To identify investable businesses, look for those with a minimum of $1,000,000 in EBITDA for transferrable businesses or $2,000,000 in profit for personality-based businesses. Additionally, consider companies with product-market fit, growth, and cash flow. The goal is to work with established businesses and scale them, rather than incurring the cost of trial and error and iteration.

    • Identifying growth requirements and capabilities in businessesInvesting in businesses requires identifying unique growth needs and capabilities. For some, like accounting firms, profits can be reinvested. Others, like brick-and-mortar chains, need significant capital. Lack of leadership talent can hinder growth, so bringing in new talent and diverse expertise is crucial.

      Successful investing in businesses involves identifying companies with different growth requirements and capabilities. Some businesses, like accounting firms, have low capital expenses and can reinvest profits into growing the business. Others, like brick-and-mortar chains, require significant capital expenditures to expand. The process of providing value to these companies involves identifying the biggest issue that will grow the business (the "what") and finding the right team to implement the solution (the "who"). At companies of a certain size, a lack of leadership talent can hinder growth and prevent founders from effectively scaling their businesses. To address this, it's essential to bring in new talent and build a team with diverse knowledge and expertise to maximize the potential of the company.

    • Focus on the fundamentals of business functionsSuccessful businesses require a balance of exceptional product, marketing, sales, and operations. Neglecting other areas can hinder growth. Implement proven strategies and focus on the basics to achieve significant growth.

      While founders often have personal strengths that help them build their businesses, it's essential to recognize that a successful business requires a balance of all key functions, including exceptional product, marketing, sales, and operations. The mistake many entrepreneurs make is focusing solely on their strengths and neglecting other areas. However, even if you're an expert in sales and marketing, for example, your business still needs a strong product and effective customer service to grow. By implementing proven strategies and playbooks in each department, you can achieve significant growth through focusing on the fundamentals. Remember, "fancy fails, simple scales." It's not necessary to create complex solutions; instead, focus on the basics and ensure they are executed effectively. At Holdco, we employ Subject Matter Experts in various departments to build up each aspect of the business, from marketing and sales to customer success, IT, finance, and more. By recognizing the importance of a well-rounded business strategy and focusing on the fundamentals, entrepreneurs can overcome constraints and drive growth.

    • Mastering core fundamentals for business growthTo build a successful business, focus on generating demand, converting sales, ensuring customer success, utilizing data effectively, and managing legal, finance, and HR functions.

      Building a successful business requires a clear understanding and implementation of core fundamentals across various functions. These fundamentals include generating demand through various channels, converting that demand into sales, ensuring customer success, utilizing data effectively, and managing legal, finance, and HR functions. By mastering these areas, businesses can increase customer value, make informed decisions, and ultimately scale without relying on acquisitions. Whether it's through cold calls, content, or partnerships, the key is to have a solid foundation in place to maximize growth. Additionally, having experts in each area to implement and scale the knowledge is crucial for businesses looking to succeed at a larger scale.

    • Importance of finance function and accurate reporting for informed business decisionsInvesting in a finance team and accurate financial reporting is crucial for making informed business decisions, especially for growing companies. Effective leadership and HR strategies are also essential for attracting and influencing talented individuals to help build and grow the enterprise.

      Having a solid finance function and accurate financial reporting is crucial for making informed business decisions, especially for growing companies. The speaker shared an experience where a founder was struggling to determine how much to invest based on volatile cash flow due to extended payment terms. The lack of financial data and expertise led to a feeling of uncertainty. The speaker also shared a personal experience of not understanding tax requirements and facing a large, unexpected tax bill. These examples illustrate the importance of having a finance team and accurate financial reporting. Additionally, the speaker emphasized the value of investing in HR, particularly in recruiting and developing valuable people to build and grow a company. From a leadership perspective, effective leadership is essential for growing a business and attracting and influencing talented individuals to help build and grow the enterprise.

    • Unlocking Employee Potential through Effective LeadershipOlder entrepreneurs, self-aware founders, and strong leadership contribute to unlocking employee potential and driving business growth. McKinsey study shows equal contribution of coaches and CEOs to team growth. Prioritize leadership development and create a culture of alignment for significant growth.

      Effective leadership, particularly in unlocking the full potential of employees, is a key driver of enterprise value. Older entrepreneurs, who may not fully understand the technology behind their businesses but excel in understanding people, can still run successful tech companies. A McKinsey study found that the contribution of coaches to team growth is equal to that of CEOs, emphasizing the importance of strong leadership in creating a culture that unlocks discretionary effort from employees. Self-aware founders who recognize their strengths and weaknesses can bring in complementary leaders to help grow their businesses. Companies that prioritize leadership development and create a culture of alignment can see significant growth, with the difference in performance being 10x or more. Cash flow and low capital expenses are also important indicators of healthy businesses that Holdco looks for when investing.

    • Understanding the Importance of Cash Flow for Business GrowthCash flow is vital for businesses to weather financial hardships, invest in growth, and increase value through customer acquisition, retention, and risk reduction.

      Cash flow is crucial for businesses as it acts as a safety net during tough times and enables opportunities for growth. Cash flow is essential for spending and selling your way out of problems, and its absence increases the risk of business failure. With cash flow, businesses can reinvest in growth through organic means or acquisitions. Growth can come from acquiring new customers, increasing the value of existing customers, or reducing risks. Companies with consistent growth and stable cash flow are more valuable as they offer a higher degree of confidence for future profits. Therefore, focusing on cash flow and implementing strategies for growth in these areas can lead to long-term success.

    • Reducing risks increases business valueEliminating key man risk, customer concentration, and financial risk can significantly boost a business's value. Founders who prioritize and stay focused on a specific avatar and problem can also increase value by capturing a larger market share at higher LTVs.

      Derisking a business and increasing its likelihood of continued success can significantly increase its value, even if it doesn't necessarily change the top or bottom line. This can be achieved by eliminating key man risk, customer concentration, and financial risk. For example, a company with $2 million in profit may be valued at $5 million using a 2.5x profit multiple. But if the profit is increased to $5 million and the business receives an 8x multiple, the overall value becomes $40 million. Focused founders who can effectively prioritize and allocate resources to serve a specific avatar and solve a specific problem are also crucial for a company's success and growth. By staying focused, founders can avoid distractions and ensure they are capturing the highest percentage of the market at the highest LTVs.

    • Focusing on a specific customer avatarIdentifying and catering to a specific customer base can lead to significant business growth, even if it means making tough decisions and potentially sacrificing short-term income.

      Focusing on a specific customer avatar, even if it means letting go of a larger customer base, can lead to significant business growth. This was demonstrated in a company where 85% of customers were less valuable but required more resources, while the remaining 15% were more valuable but required less resources. The founder, with the investors' support, made the difficult decision to shift the business to cater exclusively to the valuable 15% avatar. The result was a customer lifetime value increase from $6,000 to $75,000 and higher response rates to advertising despite a smaller audience. This lesson underscores the importance of identifying and catering to a specific customer base, even if it means making tough decisions and potentially sacrificing short-term income. Entrepreneurs often hesitate to make such changes due to fear of financial instability, but trust in the process and belief in the long-term potential can lead to substantial growth.

    • Gain outside perspective for business growthBringing in an outside investor or advisor can provide valuable insight and help avoid plateauing, ultimately leading to significant growth

      Having an outside perspective can help business growth by providing logical advice and allowing for a broader time horizon. This is based on the Solomon paradox, which shows that people often give better advice than they follow due to emotional detachment. By bringing in an outside investor or advisor, a business owner can gain valuable insight and avoid plateauing at a certain level. This can ultimately lead to significant growth and the achievement of larger goals. Additionally, it's important for business owners to redefine their definition of progress and focus on long-term growth rather than short-term gains.

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