HoldCo Builders

David Dowda, Founder and CEO of Dowda Holdings, jumped from a grueling insurance career to purchasing a $30k beach business using seller financing. He talks about rolling up various small businesses into his portfolio, including a surf shop turnaround into a coffee hotspot. With no construction experience, he successfully flipped a remote company for a 300% return. David emphasizes the importance of team-building, financial oversight, and nurturing trust while scaling businesses, advocating for sustainable growth over quick profits.

Discover the secrets behind generating 20-40% annual returns through strategic acquisitions of small, niche companies. Learn how bottom-up diversification outperforms larger deals, and why owning multiple firms enhances resilience. Delve into the 7-7-7 structure for managing numerous subsidiaries and explore the importance of maintaining culture over forced synergies. With real-world examples of impressive returns, this discussion offers practical tips for private buyers looking to thrive in the acquisition landscape.

Cyrus Hessabi, an investor-operator with a rich background in aerospace engineering and venture capital, shares insights on transitioning from VC to private equity at Shore Capital Partners. He discusses how AI is revolutionizing traditional service industries, revealing that ripe opportunities exist in sectors like property management and accounting. Cyrus defines AI-enabled services as transformational tools rather than replacements and emphasizes the importance of evaluating founder capabilities. His journey illustrates the blend of optimism and discipline essential for success in this evolving landscape.

Explore groundbreaking insights from recent Yale data on investor outcomes. Discover why access is the key factor in achieving exceptional returns, rather than mere modeling. Mikk highlights the stark discrepancy between optimistic projections and real-world investor results. The discussion uncovers the rarity of high returns, with only a small fraction of deals driving profits. Understand how elite investors navigate the landscape and why the common strategy of 'spray and pray' often falls short. Get ready to rethink your approach to investment success!

Sequoia Borgman, Founder and CEO of Borgman Capital, has had an impressive career in private equity, focusing on founder-led businesses. He shares insights on sourcing off-market deals in second-tier cities and the challenges of managing founder transitions. Sequoia also discusses the advantages of raising capital from retail investors instead of institutions, emphasizing the value they bring beyond just money. Additionally, he highlights the current landscape of private equity, navigating fewer deals and the importance of a strong team in this sector.

Akshay Ramachandran, a retired family office investor and advocate of buy-and-hold strategies, shares his journey from Wall Street to spirituality. He delves into the intricacies of his analysis framework, highlighting his success with Carvana and the importance of thinking long-term. Akshay discusses the balance between financial acumen and Buddhist practices, revealing how meditation transformed his investment perspective. With insights on defining retirement and when to sell, he blends the worlds of finance and spirituality, offering a unique outlook for aspiring investors.

Explore the fascinating world of RÖKO, a $2B holding company with 29 diverse businesses thriving on high margins and asset-light strategies. Discover founder Fredrik Karlsson’s remarkable journey from Lifco CEO to orchestrating rapid growth with a lean team. Learn about their disciplined capital allocation, commitment to profitable acquisitions, and unique operational model that thrives without micromanagement. From risks like recessions to lessons from past mistakes, this discussion unravels the secrets behind successful compounding in business.

Ian Rickwood, Founder and CEO of Henley Group, has an impressive track record deploying over $4 billion in private equity and real estate. He dives into scaling successful businesses, from car washes to food chains, and the importance of site selection using AI. Ian shares insights on partnership dynamics with his spouse and children while emphasizing resilience in entrepreneurship. He candidly discusses handling tough deals and what traits make a great operator partner, all while learning from past successes and failures.

Explore the underrated power of listening in business acquisitions. Discover how Warren Buffett built trust to close a $60M deal and learn from Shopify's success in prioritizing empathy. Understand the importance of conversational cues that can reveal hidden deal signals. Gain insights into how persistent relationship-building can outshine even the best financial offers. Finally, uncover practical tips for mastering listening during due diligence while cultivating rapport with sellers.

In this engaging discussion, Joel Mathew, the Head of Originations at Woodson Equity, shares his entrepreneurial journey leading to private equity. He outlines Woodson's unique focus on diversified industrials and emphasizes the importance of control investments and hands-on operations. Joel reveals his playbook for sourcing over a thousand deals annually, the significance of company culture, and strategies for effective value creation. He also discusses the excitement in lower middle-market opportunities stemming from current market volatility.