HoldCo Builders

Ben Wolff, co-founder of Oneira, has transitioned from a tech consultant to a real estate mogul, managing over $65 million in assets. He discusses his impressive journey from $30,000 in debt to generating $1.7 million annually. With industry-leading margins of 52-55% NOI, he reveals how social media helps secure direct customer relationships and enhance bookings. Ben emphasizes the importance of quality, sharing lessons learned, and the power of public engagement in building a brand. His insights exemplify innovative strategies for success in hospitality.

Rafael Quinn, co-founder of Alternative Holdings, shares his remarkable journey from selling everything at 26 to building a $127 million portfolio. He emphasizes the importance of investing in companies you understand and collaborating with great people. The conversation dives into the significance of cash flow, strategic acquisitions, and the lessons learned from his zero-deal period. Rafael also reflects on balancing family life with business growth and the role of luck in success, making it an inspiring tale for budding entrepreneurs.

Michael Cassau, founder of Grover and former Goldman Sachs analyst, shares his journey from finance to founding a billion-dollar tech subscription company. He discusses the intricacies of raising hundreds of millions, emphasizing the importance of a compelling narrative and investor relationships. Cassau reveals lessons learned from Rocket Internet, the challenges of early startup life, and the significance of high energy in driving results. With humor, he recounts fundraising stories and reflects on the balance of work and personal life.

Ujwal Velagapudi, a 32-year-old entrepreneur, runs a lucrative vending empire called UV Holdings with thousands of machines. He shares his journey of building an 8-figure EBITDA holding company without prior experience, often working just 3-4 hours a week while traveling the globe. Ujwal discusses how he funds acquisitions, manages operations single-handedly, and automates business functions. His key takeaway? "Just go and do it!"—an inspiring mantra for aspiring entrepreneurs looking to break into the business world.

Mathias Calonius, co-founder of the Finnish holding company JATKAJA, discusses his journey in acquiring four companies and building a $30 million portfolio in just four years. He shares insights on finding excellent deals, avoiding costly mistakes, and the patience required in managing diverse businesses. Mathias emphasizes the significance of relationship-building with CEOs during transitions and outlines strategies for tripling revenue from $3 million to $9 million. His experiences provide a fascinating look at the strategic dynamics of entrepreneurship and growth.

Michael Bjorn Huseby is an investment fund formation attorney at DLA Piper, representing both fund sponsors and investors. He dives into the critical role of side letters and the complexities of waterfall arrangements in investment funds. The conversation highlights why investors avoid novel approaches, instead favoring familiar structures. Huseby shares insights on how GPs can build trust with LPs and addresses the challenges of first-time fund managers, emphasizing the importance of transparency, communication, and adapting to regulatory changes.

In this engaging conversation, Andy Schornack, CEO of Flagship Bank and President of Security Bank and Trust Company, shares his journey from aspiring entrepreneur to banking leader. He reveals the secrets behind building two banks to a billion-dollar total in assets. They discuss the real reasons behind people's distrust of bankers and the importance of transparency in community banking. Andy also dives into the challenges small business owners face when seeking loans, and why traditional banks still hold an edge over fintech. His insights on building relationships and the future of banking are both refreshing and thought-provoking.

Val Katayev, a serial entrepreneur with over $100M in profits, shares his journey of building businesses in digital media and real estate. He discusses strategies for scaling companies to $10M and $100M, emphasizing the significance of distribution networks. Val reveals how he successfully raised millions for asset management and dives into the evolution of peer-to-peer lending. He highlights the importance of team dynamics, the need for innovation in the jewelry industry, and reflects on his evolving relationship with money.

Justin Mazeka Vogt, co-founder and CEO of Evermore Industries, shares his journey from Bain Capital to building a permanent capital holding company. He discusses the importance of complementary skills in partnerships and the strategic focus on long-term value over dividends. Justin reveals his thoughts on investor-advisors and the significance of team dynamics for post-acquisition growth. He also highlights the role of Twitter in fostering entrepreneurial communities and shares powerful insights on decision-making in business.

Alec Torelli, a high-stakes poker pro with over $2.2 million in winnings, shares his dual passions for poker and investments. He discusses his decision-making process in asymmetric investments and the importance of cultivating a winning mindset. Alec reflects on the emotional impacts of gambling in Macau and balances his poker career with personal growth. He emphasizes resilience after setbacks and offers insights on networking within the poker community to fuel business ventures. His journey from poker champion to investment strategist reveals the psychology behind both worlds.