Search Funded: The ETA Podcast

Jordan Blackwell is the co-founder and CEO of Siah Labs, an AI implementation company focused on helping small businesses reduce owner dependence, streamline operations, and preserve institutional knowledge.A graduate of Georgetown University, Jordan built his career in sales and technology, including roles at two Y Combinator-backed startups, before transitioning into software engineering. He launched Siah Labs in 2024 when customers of his previous employer approached him to build solutions for their businesses. He has since been joined by his wife, Deanna, a former Amazon UX designer.Jordan sees AI as an important tool for addressing one of the biggest challenges facing American small businesses: ensuring that the value owners have spent decades building isn't lost when they retire.In this episode, we discuss:Jordan's transition from sales to software engineering and entrepreneurship, and what he's learned building a business with his wifePractical examples of how AI, automation, and better data management can transform small business operations, including one client whose COO went from working 60 hours a week to three daysWhy reducing owner dependence and preserving institutional knowledge are critical to successful business successionHow AI and the coming wave of small business ownership transitions could create opportunities for economic mobility in cities like PhiladelphiaWhat acquisition entrepreneurs should look for when evaluating businesses for potential AI implementationWhy AI isn't always the right solution, and why getting the fundamentals of data management right is often more importantSend us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

Teniola Tayo is a Nigerian economic development and policy expert who recently graduated from Duke’s Fuqua School of Business. Before business school, she founded Aloinett Advisors, an advisory practice focused on trade, investment and economic development in Africa, and worked with organizations including the Office of the Vice President of Nigeria, the World Bank and the Africa Policy Research Institute.Her own experience as a young entrepreneur, combined with seeing viable Nigerian businesses dismantled when their owners emigrated, led her to begin exploring a different model for entrepreneurship through acquisition in Africa: “micro-ETA,” focused on businesses worth as little as $10,000 to $50,000. Her research on the idea has since been featured by the World Economic Forum.In this episode, we discuss:Why Africa needs to focus not only on creating new businesses, but also on preserving viable businesses when their owners retire, relocate or step awayHow micro-ETA could create an acquisition market for businesses in the $10,000–$50,000 range, and why Teniola believes these deal sizes could be accessible to both local professionals and members of the African diasporaThe industries showing the most interest from prospective buyers, including food businesses, salons and private schoolsHow micro-ETA could redirect diaspora capital and remittances toward productive investment while potentially giving Africans abroad a pathway to eventually return homeSend us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

Daniella Devine grew up around Peacock Floors, a commercial flooring business her family has operated in San Francisco for more than four decades. But rather than simply inheriting the company, she built a career of her own before eventually returning and purchasing the business from her father.Despite knowing the business and industry intimately, her first year as an owner proved far more difficult than expected. Customer volumes shifted, the operational transition consumed more time and capital than anticipated, a partnership went wrong, financing costs climbed, and at one point Daniella believed the business could be only months away from failure.She ultimately turned the business around by returning to sales, restructuring the company’s debt, making difficult personnel decisions, and bringing in an experienced executive coach who helped her build the systems, leadership practices and operating discipline the business needed.In this episode, we discuss:Why Daniella initially chose not to enter the family business, and what eventually convinced her to come back and buy itWhy historical financial performance can give buyers false confidence, and how long-standing customers can behave very differently after an acquisitionHow debt service, working capital and the cost of growth can make the first year after an acquisition much harder than buyers expectThe mistakes that led Daniella into a 24% interest-only bridge loan, a difficult partner situation and a period where she feared the business could failHow bringing in an experienced executive coach helped her shift from survival mode into execution mode and make faster, less emotional decisionsWhat family members and employees should consider before trying to succeed an existing owner, including family dynamics, valuation, financing and replacing the roles family members currently performHow Daniella financed acquisitions using a combination of bank debt, seller financing and borrowing against her own retirement assetsSend us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

 Ian Reynolds began his ETA journey in 2017, initially pursuing a traditional search before pivoting to a self-funded acquisition of Zibtek, a software services company he operated alongside its founder. After several years as an operator, he went on to build Thesis Capital, which has now invested across more than eight portfolio companies and closed over $100 million of transactions. Thesis has developed a differentiated model around identifying experienced operators first, building investment theses around their expertise, and providing the sourcing, transaction and capital infrastructure around them.In this episode, we discuss:What Ian learned from acquiring and operating Zibtek, and how those lessons shaped the way Thesis invests todayWhy Thesis takes a “people first” approach, identifying experienced operators before searching for businesses that fit their backgrounds and strengthsWhat Ian looks for in operators, including the behavioral traits he believes matter more than traditional M&A experienceHow Thesis reduces some of the career and opportunity-cost risks that come with pursuing a traditional searchWhy service, alignment and long-term thinking are central to the way Thesis approaches business ownershipHow Ian thinks about choosing equity and debt partners, and why how a capital provider behaves when things go wrong matters more than their terms when everything is going wellWhy governance and fiduciary responsibility are especially important in the often informal lower-middle marketHow increasingly competitive sourcing, longer search timelines and changing market conditions are affecting ETAWhy Ian believes buyers should stay close to industries they actually understand rather than pursuing attractive businesses outside their expertiseWhy overpaying may be one of the biggest mistakes in ETA, and why buyers should focus on actual free cash flow rather than getting caught up in EBITDA multiples or deal feverSend us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

Chaitanya Rathi has spent two decades as an operator, entrepreneur and investor in India. He helped build Sula Vineyards’ wine tourism business, later returned as COO and helped take the company public, and in between worked in both private equity and venture capital, investing in and helping build consumer businesses across India. He eventually began exploring an acquisition of his own, discovered ETA, and instead decided to build Searchlight ETA, becoming the first dedicated search fund investor in India.In this episode, we discuss:Why he believes India could follow the same trajectory in search that it did in private equity and venture capitalHow Indian business owners view search funds differently from traditional private equity, particularly around succession and preserving their legacyWhy financing acquisitions remains one of the biggest challenges for Indian searchers, and how the capital stack differs from the USWhere he sees the most attractive opportunities, including regulated SaaS, precision manufacturing and export-oriented businessesWhat he has learned from India’s first wave of searchers and acquisitions, and why getting the first few deals right is critical to building the ecosystemHow India’s combination of aging business owners, returning diaspora talent and long-term economic growth could create a major opportunity for ETA Send us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

Kevin Fleming left Wharton during COVID to pursue an unconventional search thesis: combining ETA with his background in real estate private equity.In this episode, we discuss:Why Kevin chose independent hotels despite their asset intensity and operational complexityHow he financed Avenir Hospitality’s first acquisition in Cannon BeachWhat he learned going from investor to hands-on operatorWhy Avenir focuses on supply-constrained leisure markets and independent hotelsHow the strategy has evolved as Avenir expanded across the West Coast, including its recent Joshua Tree acquisitionThe economics and tax advantages of hotel investing, including cost segregation and bonus depreciationSend us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

In this episode of Search Funded, we sit down with entrepreneur, investor, and holdco founder Vadim Rogovskiy to explore one of the most important emerging trends in entrepreneurship through acquisition: the intersection of AI and small business ownership.Vadim shares his journey from building and scaling venture-backed startups, including AI company 3DLOOK, to founding Rebel Capital, a holdco focused on acquiring and modernizing software businesses with AI. He explains why more founders and investors are becoming interested in acquisitions and cash-flowing businesses, and how ETA offers a compelling middle ground between operating a single company and being a passive venture investor.The conversation dives into practical applications of AI for acquisition entrepreneurs, including how AI can uncover missed revenue opportunities, capture institutional knowledge trapped in inboxes and spreadsheets, improve sales operations, and automate project management workflows. Vadim also discusses lessons learned from hosting his popular AI for Rollups & Holdcos events, why AI may favor serial acquirers and holdcos, and how the next generation of acquisition entrepreneurs can prepare for an increasingly AI-driven future.Whether you're a searcher, independent sponsor, holdco operator, or simply curious about how AI is changing the economics of business ownership, this episode offers a practical look at where the industry may be heading next.Send us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

 In this episode of Search Funded, we are joined by Nikita Gossain, founder and principal of PPR Capital, an Australian investor who has acquired, operated, and exited small businesses through a permanent-hold acquisition model focused on durable, founder-led companies.Nikita shares her path from KPMG, where she worked on large acquisitions, IPOs, and complex transactions, into the much more personal world of small business ownership. After completing her MBA at Cornell, she set out to raise a traditional search fund in Australia, but the ecosystem was still early and investors wanted to see the model proven locally. Rather than waiting, she began searching anyway, cold calling business owners before acquiring Smokeshield, a 40-year-old electronic security business, using her own capital and a personally guaranteed bank loan.The conversation explores why small business acquisitions require a different lens from large corporate transactions. Nikita explains how the mechanics of M&A still translate, from diligence to working capital to deal documentation, but the real risks often sit in people, culture, undocumented knowledge, and founder dependency.She discusses:Why she was drawn to ETA after growing up around small businessWhat her KPMG transaction experience taught her about acquisitionsWhy Australia remains early in its ETA ecosystemWhy she believes the risk of enduring small businesses is often overstatedHow she thinks about buying businesses that can remain relevant 20 years from nowWhy PPR is built around long-term ownership rather than a five-year exitHow her yield model works through prudent leverage and dividendsWhy growth at all costs can damage certain founder-led businessesHow she thinks about replacing founders with the right CEO or general managerWhy founder dependency can be an opportunity rather than only a riskWhat operating Smokeshield taught her about culture, systems, and change managementHow charity ownership could create a new succession path for enduring small businessesWhy her exposure to poverty in India shaped her commitment to global health and effective givingNikita also shares her view that many good small businesses are not meant to be transformed, rolled up, or pushed into aggressive growth. The better path may be to preserve what already works, improve it carefully, and let the business compound over decades.Whether you’re interested in ETA outside the U.S., permanent-hold acquisition models, small business succession, or the intersection of business ownership and philanthropy, this episode offers a thoughtful look at a very different way to buy and steward enduring small businesses.Send us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

In this episode, Nick speaks with veteran M&A attorney Joel Ankney, author of Here's the Deal: Everything You Wish a Lawyer Would Tell You About Buying a Small Business. Joel shares his journey from Big Law attorney to running a boutique practice focused on small business acquisitions and explains how an unexpected call from a professor introduced him to the emerging world of entrepreneurship through acquisition. Drawing on more than three decades of transaction experience and roughly 125 self-funded ETA deals, Joel discusses how the search ecosystem has evolved from a niche concept into a mainstream path to business ownership. He explains why he is seeing more searchers raise outside capital, how that trend is changing deal structures, and the additional risks and complexity that come with investor-backed acquisitions. The conversation focuses on the questions first-time buyers most frequently ask lawyers: when to hire counsel, what lawyers actually do during a transaction, how due diligence should be approached, how long deals really take to close, and what buyers should expect to pay. Joel shares practical examples of mistakes he has seen in letters of intent, why engaging a lawyer early can save significant money and headaches later, and how legal issues can derail a transaction if they are not addressed upfront. Joel also discusses the role of AI in dealmaking, the importance of state-specific legal knowledge, how lawyers and accountants should work together during diligence, and the characteristics of the most successful acquisition entrepreneurs he has worked with. For anyone considering buying a small business, this episode provides a practical roadmap for navigating the legal side of acquisitions and avoiding some of the most common mistakes first-time buyers make. Send us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube. 

In this episode of Search Funded, I speak with Bhavik Rasyara, founder of Pravah Capital and one of the first searchers helping build the entrepreneurship through acquisition ecosystem in India.Bhavik shares his journey from IIT Madras to BCG, Bain Capital, Scaler, and Harvard Business School, and explains why he entered his MBA already knowing he wanted to return to India and become an entrepreneur. He also discusses why the VC-backed startup path did not fully resonate with him, and why ETA felt more aligned with his desire to build durable businesses over the long term.We discuss what has surprised him since he started searching in India, including the depth of the intermediary ecosystem, the volume of actionable deal flow, and the challenges around seller valuation expectations. Bhavik also explains why India differs from the U.S. search market, particularly around acquisition financing, seller involvement, growth expectations, and exit opportunities.Finally, Bhavik shares the types of businesses he is most interested in, why B2B services and technology are attractive areas in India, and how he sees the Indian ETA ecosystem developing over the next decade.Send us Fan MailSupport the showFind us on Apple, Spotify, Amazon, and YouTube.