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Recent Episodes

February 7, 2024
From Big Law to Boutique Firm: Focusing on SMB and HoldCo's with Josh Lowenthal
<p>Josh's Twitter: @joshualowenthal<br/>Will's Twitter: @williamtgoodson<br/><br/>Josh Lowenthal, owner and founder of the Law Office of Joshua A. Lowenthal, PLC shares his thoughts and expertise in tax, law, and building HoldCo’s through SMB acquisition on this episode. We discussed his background in public accounting and working with large firms before starting his own firm. Josh's primary client base is small and solo entrepreneurs building seven & eight figure business empires. <br/><br/>During the conversation, Josh emphasizes the importance of entrepreneurship and the potential for financial freedom. He highlights the benefits of buying small and medium-sized businesses (SMBs) and building holding companies as a viable path for individuals to achieve their dreams and create wealth. He explains that by acquiring and scaling SMBs, individuals can create job security, build equity in assets, and achieve financial success.<br/><br/>Josh also discusses the concept of the "new American dream" and challenges the traditional notion of a career-long W-2 job. He encourages listeners to think beyond the traditional path and consider the opportunities in entrepreneurship and holding companies. He believes that by starting early and taking control of their own destiny, individuals can create a life and career that offers more than the traditional path.<br/><br/>Overall, this episode offers valuable insights into the world of tax and business law, entrepreneurship, and the potential of buying SMBs and building holding companies as a real path in the modern economy. It challenges conventional career paths and encourages listeners to consider alternative routes to achieve their goals and aspirations.<br/><br/>00:00:20 - Introduction to Josh Lowenthal<br/>00:00:31 - Goals for Entrepreneurs<br/>00:00:52 - Business Governance and Tax Planning<br/>00:01:13 - Background in Public Accounting<br/>00:02:06 - Transition from KPMG to Law Firm<br/>00:03:04 - Importance of Estate Planning for Business Owners<br/>00:04:04 - Big Law Experience and Work-Life Balance<br/>00:05:03 - Differences in Big Four and Big Law<br/>00:07:06 - Decision to Start Own Law Firm<br/>00:08:15 - Entrepreneurship vs. Being Self-Employed<br/>00:09:21 - Current Scale and Future Goals of the Business<br/>00:12:04 - Lifestyle and Impact Goals<br/>00:13:36 - Defining Freedom and Entrepreneurship<br/>00:15:10 - Corporate America vs. Entrepreneurship<br/>00:17:01 - Achieving Financial Freedom Through Entrepreneurship<br/>00:18:03 - Surprising Lack of Entrepreneurial Consideration Among Peers<br/>00:20:10 - The Realities of Entrepreneurship and Wealth Building<br/>00:21:12 - Building Businesses with Friends<br/>00:22:15 - Typical Clients in Holdco World<br/>00:24:18 - Living in Smaller Cities and Networking<br/>00:25:06 - Long-Term Relationships with Clients<br/>00:26:00 - Adjusting Lifestyle and Income Expectations<br/>00:27:08 - American Dream and Career Satisfaction<br/>00:28:12 - Finding Happiness and Success in Entrepreneurship<br/>00:29:29 - The Trendiness of SMB and ETA Online<br/>00:30:17 - The Reality of Business Acquisitions and Commitment<br/>00:32:00 - Building Connections and Networks Online<br/>00:33:10 - Trendiness in SMB and ETA Communities<br/>00:34:00 - Legal and Tax Benefits of Holdco Structures<br/>00:36:07 - M&A Trends and Private Equity Movements<br/>00:38:57 - The Risks of Traditional Career Paths<br/>00:40:50 - Legal Changes and Trends in Client M&A Activities<br/>00:41:30 - Structuring Businesses for Legal and Tax Advantages<br/>00:44:25 - Benefits of Holding Company Structures<br/>00:46:50 - Private Equity Trends in Lower Middle Market<br/>00:47:53 - Advice to Younger Self: Start Earlier<br/>00:52:52 - How to Connect with Josh Lowenthal</p>

January 31, 2024
Building a $100m Holding Company: The Journey of Rafael Quinn, Co-Founder of Alternative Holdings
<p>Rafael's Twitter: @rafaquinn<br/>Will's Twitter: @williamtgoodson<br/><br/>Rafael Quinn, co-founder of Alternative Holdings, a holding company that just surpassed $100m in revenue in 2023, shares how he got his start in business and investing, how he found, acquired, and operated Alternative Holdings' first business, and how that grew into the large multinational portfolio of private companies they are today.</p><p>Throughout the conversation, Rafael emphasizes the significance of prudent leverage and the need to focus on cash flow rather than just EBITDA. He also shares some of the lessons he learned from their early experiences, including the importance of management continuity and the value of gut instincts in decision-making. We also get to hear some of Rafael’s more crazy stories from running and operating businesses.</p><p>There is also brilliant life and career advice shared toward the end of the episode. Overall, this episode offers valuable insights into the world of holding companies, entrepreneurship, and the key factors that contribute to their success.<br/><br/>[00:01:00] Baseball card business passion.</p><p>[00:07:27] Servicing debt and cashflow.</p><p>[00:08:27] Importance of cashflow.</p><p>[00:13:30] Frugal thinking in businesses.</p><p>[00:17:28] Investing in any industry.</p><p>[00:21:06] Stepping into the CEO role.</p><p>[00:24:17] Building a holding company.</p><p>[00:29:10-00:29:20] Management continuity and alignment.</p><p>[00:32:06-00:32:17] Gut feeling in dealmaking.</p><p>[00:37:47] Buying bigger for growth.</p><p>[00:41:31] Entering the US market.</p><p>[00:42:50] Making changes at the top.</p><p>[00:46:41] Business challenges and growth.</p><p>[00:50:33] Appreciating the present moment.</p><p>[00:55:08] Take risks in your career.</p><p>[00:59:14] Distractions and shiny things.</p>

December 15, 2023
From Print-on-Demand to SMS Software: Danny Guthrie's Journey in E-Commerce
<p>Danny's Twitter: @_dvniel_ <br/><br/>In this episode we speak with Danny Guthrie, the head of growth for YC-funded company OneText. OneText is an SMS software that serves e-commerce brands and has experienced significant growth over the past year. Danny has a background in e-commerce as both a brand owner and service provider, making his insights valuable for those in the SaaS and e-commerce industries. Throughout the conversation, Danny shares some excellent pointers for growth and discusses his own entrepreneurial journey. From his high school app development days to starting and scaling e-commerce brands, Danny's experiences provide valuable lessons for listeners. He also touches on the importance of giving back and incorporating charitable aspects into businesses. The episode covers various topics, including the use of AI in e-commerce, the challenges and opportunities in the industry, and the future of DTC brands. Overall, this episode offers valuable insights and advice for anyone interested in the growth and success of e-commerce and SaaS companies.</p>
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