Ep. 24- Self-Funded Search, Deal Structures & Red Flags: Jacob Hall on Investing in Small Businesses
In this interview, Sean Smith (Managing Partner of Search Fund Ventures & Founder of SMB Investor Network) sits down with Jacob Hall, Founder of Kando Capital, to explore the fundamentals of investing in small businesses through self-funded search and independent sponsor deals.Jacob shares his unique path from Fortune 500 operator to fund manager, his “buy box” criteria, and the red/yellow flags that investors should watch for when evaluating opportunities. The conversation dives deep into:Why operational experience matters more than Wall Street backgroundsHow to define and evolve your investment “buy box”Revenue quality, customer concentration, and key-person riskCreative deal structures: forgivable seller notes, earn-outs, rollover equityHR diligence, culture, and compensation as overlooked risksAligning sellers, buyers, and investors for long-term successThis is a must-watch for anyone interested in search funds, small business acquisitions, or creative capital structuring in the lower middle market.👉 Subscribe for more interviews with SMB investors and operators.👉 Leave your thoughts or experiences in the comments below.Connect with the speakers:🔗 Connect with Jacob Hall: https://www.linkedin.com/in/jacobhall01/🌐 Kando Capital: www.KandoCapital.com🔗 Connect with Sean Smith: https://www.linkedin.com/in/sean-smith-47ab2a70/🌐 SMB Investor Network: https://www.smbinvestornetwork.com/
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Ep.23- The LP Playbook: Pascal Wagner on Cash Flow Investing Across Asset Classes
In this episode, Sean Smith (Managing Partner of Search Fund Ventures & Founder of SMB Investor Network) sits down with Pascal Wagner, founder of Grow Your Cash Flow and seasoned LP investor.Pascal shares his journey from working with the investment team at Techstars, one of the world’s top accelerators, to building a multi-asset-class cash flow strategy. From helping his family secure financial independence to reviewing 2,000+ deals and investing across real estate, private credit, self-storage, oil & gas, and retail development, Pascal lays out his playbook for LP investing.Key topics include:Why every LP needs a macro plan before reviewing deals.How to vet operators and spot red flags that others miss.The trade-offs between emerging managers and institutional funds.Tax strategies and incentives that boost returns.Why operator consistency beats flashy pro formas.If you’re exploring passive investing, LP strategies, or alternative assets, this conversation is a must-watch.👉 Subscribe for more interviews with leading voices in SMB and alternative investing.💬 Share your thoughts in the comments — how do you approach cash flow investing?Connect with the speakers:Pascal Wagner LinkedIn: https://www.linkedin.com/in/pascalwagner/Grow Your Cash Flow: http://growyourcashflow.ioPassive Investing Starter Kit: https://passiveinvestingstarterkit.comSean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/SMB Investor Network: https://www.smbinvestornetwork.com/
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Ep.22- The Art & Science of Quality of Earnings: Mitch Petracca on SMB Deals, Tech, and Diligence
In this in-depth conversation, Sean Smith (Managing Partner, Search Fund Ventures & Founder of SMB Investor Network) sits down with Mitch Petracca, CPA and Founder of Forward Firm, to unpack the art and science of Quality of Earnings (QoE) in small business acquisitions.Mitch shares his journey from PwC to founding Forward Firm, where he supports searchers, independent sponsors, and small private equity firms on deals from $1M–$50M EV. Together, Sean and Mitch explore:How technology and automation are transforming the diligence processThe balance between quantitative rigor and the “art” of working with sellersA practical framework for evaluating EBITDA adjustments (tiers of certainty vs. subjectivity)The critical role of working capital in ensuring post-close successReal-world stories from QoE engagements—what investors should look out for.Whether you’re an investor, operator, or service provider in the SMB ecosystem, this discussion offers actionable insights into deal-making, risk management, and value creation.👉 Subscribe for more interviews with leading voices in SMB investing.👉 Leave your thoughts in the comments—we’d love to hear your perspective.Connect with the speakers:Mitch Petracca (Forward Firm): https://forwardfirm.com/Mitch Petracca LinkedIn: https://www.linkedin.com/in/mitchpetracca/Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/SMB Investor Network: https://www.smbinvestornetwork.com/
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Ep. 21- Tax Structuring & Diligence in SMB M&A | Sean Smith & Roman Basi
In this episode, Sean Smith, Managing Partner at Search Fund Ventures and founder of the SMB Investor Network, sits down with Roman Basi, Managing Partner of Basi & Basi, Attorneys & CPAs.Roman brings nearly three decades of experience advising on mergers, acquisitions, and tax structuring. Together, they break down the critical aspects of tax diligence in SMB transactions — from entity selection (C-Corp, S-Corp, LLC) to advanced structuring tools like QSBS (Section 1202), F Reorganizations, 338(h)(10) elections, and personal goodwill strategies.Key discussion points include:Why tax diligence is essential in SMB acquisitionsThe risks of bad S-Corps and how to avoid themHow to mitigate post-close tax liabilitiesStrategies to minimize double taxationStructuring to maximize value for buyers and sellersInsights on the new tax bill and its impact on investorsThis conversation is a must-watch for investors, operators, and advisors navigating the SMB acquisition ecosystem.👉 Subscribe for more interviews with SMB dealmakers and experts.👉 Share your thoughts in the comments below — what tax diligence questions do you want answered?Connect with Roman Basi & Sean Smith:The Center for Financial, Legal & Tax Planning, P.C.– https://www.taxplanning.com/Roman Basi LinkedIn - https://www.linkedin.com/in/roman-basi-/Sean Smith LinkedIn - https://www.linkedin.com/in/sean-smith-47ab2a70/SMB Investor Network – https://www.smbinvestornetwork.com/
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Ep. 20- Women Driving the Search World: Beki Darlin’s Dealmaker Playbook
In this episode, Sean Smith, Managing Partner at Search Fund Ventures and Founder of SMB Investor Network, sits down with Beki Darlin, growth partner, fractional CMO/CRO, and founder of Our Way (Women’s Acquisition Entrepreneur Ecosystem).Beki shares her journey from an unexpected career pivot into sales and marketing, to becoming a growth partner in search and acquisition. She explains how women are shaping the SMB acquisition landscape, the unique strengths they bring to deal-making, and the importance of community in what is often a lonely process for searchers.The discussion covers:Beki’s transition from paralegal to entrepreneur and operator.Her experience building and exiting a marketing agency, then moving into consulting for equity.The creation of Our Way, a community supporting women in ETA (Entrepreneurship Through Acquisition).Key differences in how women approach risk, negotiation, and post-acquisition operations.Real stories of female searchers who accelerated their journey to closing deals through community support.Why resilience, creativity, and collaboration are superpowers for women in the search fund ecosystem.If you’re an investor, operator, or searcher exploring SMB acquisitions—or simply interested in the evolving role of women in this space—this conversation offers both practical insights and inspiring stories.👉 Subscribe for more interviews with leading voices in the SMB investing and search fund ecosystem.👉 Leave your thoughts in the comments—we’d love to hear your perspective.Beki Darlin LinkedIn: https://www.linkedin.com/in/bekidarlin/Our Waee (Women’s Acquisition Entrepreneur Ecosystem): https://ourwaee.com/Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/SMB Investor Network: https://www.smbinvestornetwork.com/
Forget startups. Forget climbing the corporate ladder.
The real path to wealth? Owning profitable small businesses.
Hosted by Sean Smith and Nick Bryant, The SMB Investor dives into how investors, operators, and dealmakers are building wealth through small business acquisitions, syndicates, and holding companies.
We talk to the pros—fund managers, investors, searchers, and service providers—who are making SMB investing the next big asset class.
Whether you want to invest, operate, or build your own holding company, this podcast is your playbook.
Ireland