The SMB Investor

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 backgrounds
• How to define and evolve your investment “buy box”
• Revenue quality, customer concentration, and key-person risk
• Creative deal structures: forgivable seller notes, earn-outs, rollover equity
• HR diligence, culture, and compensation as overlooked risks
• Aligning sellers, buyers, and investors for long-term success

This 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/

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.io
• Passive Investing Starter Kit: https://passiveinvestingstarterkit.com
• Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/

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 process
• The balance between quantitative rigor and the “art” of working with sellers
• A practical framework for evaluating EBITDA adjustments (tiers of certainty vs. subjectivity)
• The critical role of working capital in ensuring post-close success
• Real-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/

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 acquisitions
• The risks of bad S-Corps and how to avoid them
• How to mitigate post-close tax liabilities
• Strategies to minimize double taxation
• Structuring to maximize value for buyers and sellers
• Insights on the new tax bill and its impact on investors

This 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/

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/

In this episode of the SMB Investor Podcast, Sean Smith (Managing Partner, Search Fund Ventures; Founder, SMB Investor Network) sits down with Christien Louviere, Co-Founder of BDE Capital, to explore the journey from venture capital and startup founding to becoming an independent sponsor in the lower middle market.Christien shares:- Why BDE Capital focuses 80% on healthcare and 20% on B2B services- How his team evaluates leadership, talent, and sales models before acquiring a business- The advantages of significant rolled equity in aligning seller and buyer incentives- Unique due diligence techniques using AI for scenario analysis on management teams- Lessons learned from both venture-backed exits and SMB acquisitions- Deal structure tips for independent sponsors, including equity roll, milestones, and avoiding overreliance on seller notesWhether you’re an investor, operator, or entrepreneur looking to buy and grow established businesses, this conversation is packed with actionable insights on sourcing, structuring, and scaling acquisitions.📌 Subscribe for more interviews with top SMB investors, operators, and dealmakers.💬 Leave a comment with your takeaways or questions about independent sponsor strategies.🔗 Christien Louviere on LinkedIn: https://www.linkedin.com/in/christienlouviere/🔗 BDE Capital: https://bdecap.com/🔗 Sean Smith on LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/🔗 SMB Investor Network: https://www.smbinvestornetwork.com/

In this interview, Sean Smith (Managing Partner at Search Fund Ventures) sits down with Brian Wolfe, founder of Funded Ventures, to unpack his transition from 17 years of big law to building and scaling SaaS businesses through M&A. Brian shares deep insights from his time advising major PE firms like Bain and Vista, his own SaaS roll-up exit to Alpine Investors, and his current role backing Midwest operators in ETA.

They explore the realities of subscale M&A, conviction-building in first-time operators, how to navigate deal risk and ambiguity, and the evolution of the traditional search model. Whether you're an investor, operator, or aspiring searcher, Brian offers sharp perspective on what it takes to win in today's ETA environment.

The conversation explores:07:58 The Role of Mentorship in ETA15:35 Building a Network and Professionalizing the Search23:16 Creating a Funded Operating Partner Relationship31:20 Insights on Subscale Deals and Market Dynamics

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💬 Leave your thoughts or questions in the comments — we read every one!

• 🔗 Brian Wolfe LinkedIn: https://www.linkedin.com/in/brianwolfe/
• 🌐 Funded Ventures Website: https://fundedventures.com/
• 🔗 Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• 🌐 SMB Investor Network Website: https://www.smbinvestornetwork.com/

#SearchFunds #SaaSInvesting #ETAOperators #PrivateEquityInsights #SMBDeals #LowerMiddleMarket #RollupStrategy #FundedVentures

In this episode, Sean Smith (Managing Partner at Search Fund Ventures and CEO of SMB Investor Network) sits down with Caleb Basile, CPA and founder of QoE Prep, a firm specializing in fast-turnaround buy-side Quality of Earnings (QoE) reports for the lower-middle market.Caleb breaks down what investors and operators *really* need to understand about revenue quality, working capital, and cost structure when evaluating a small business acquisition. He shares frameworks for assessing recurring revenue, customer concentration, revenue recognition, and the risks of owner-driven sales. Caleb also highlights red flags in working capital manipulation and the most common missteps in gross margin diligence.Whether you’re an investor backing searchers or a buyer diving into diligence, this is a must-watch breakdown of how financial quality drives deal outcomes.👉 Subscribe for more interviews like this.💬 Leave your takeaways or questions in the comments.🛜 Connect with Caleb:- Caleb Basile LinkedIn: https://www.linkedin.com/in/qoeprep/- QoE Prep: https://qoeprep.com/quality-of-earnings- Contact Caleb: [email protected]🛜 Connect with SMB Investor Network:- Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/- SMB Investor Network: https://www.smbinvestornetwork.com/

In this episode, **Sean Smith**, Managing Partner at **Search Fund Ventures** and CEO of **SMB Investor Network**, sits down with **Christian Ruf**, founder of **Uncommon Elite**, to unpack how elite military operators are thriving in the world of small business acquisitions.Christian shares his journey from flying helicopters in special operations to placing SEALs, Green Berets, and Rangers into leadership roles at businesses across the U.S.—from $50M HVAC companies to high-growth home services rollups. The conversation explores:- The top attributes that matter more than experience- What makes special operations veterans uniquely suited to lead SMBs- Why emotional intelligence and “compassionate tenacity” win over rigid leadership- How to vet leadership teams with better questions- Examples of successful placements, including CEOs, COOs, and integratorsIf you're an **investor, searcher, or operator** in the SMB world, this episode is a must-watch for learning how to build winning teams with unmatched resilience and adaptability.🟦 Subscribe for more interviews like thisLeave your thoughts in the comments – what traits do YOU look for in a leader?🔗 Connect with Christian Ruf: https://www.linkedin.com/in/christian-ruf-221a6728a/🔗 Learn more about Uncommon Elite: https://www.uncommonelite.com/🔗 SMB Investor Network: https://www.smbinvestornetwork.com

In this episode, Sean Smith, Managing Partner at Search Fund Ventures, sits down with **Lisa Forrest**, Head of the Self-Funded Search team at **Live Oak Bank**, to dive deep into the mechanics of SBA financing in small business acquisitions.With over **38 years in banking**, Lisa shares:- How SBA 7(a) loans are structured and why they’re a powerful tool for self-funded searchers.- Key underwriting criteria, including cash flow coverage ratios and common deal-breakers.- The rise of investor-backed self-funded deals and what investors should know about the 20% personal guarantee rule.- Real-life stories of post-close challenges—and how smart deal structuring helped borrowers succeed.You’ll also learn how Lisa and her team evaluate hundreds of deals each year, mentor searchers pre-LOI, and run **weekly SBA office hours and deal vetting sessions**.We brake dawn this episode in: 00:00 Introduction to SBA Loans and Self-Funded Search02:31 The Evolution of Self-Funded Searchers04:52 Understanding SBA Loan Structures07:47 Capital Structures in Small Business Acquisitions10:38 Underwriting Process and Debt Service Coverage13:07 Key Considerations for Lenders16:07 Cultural Fit and Management Considerations25:22 Navigating Cultural Integration in Acquisitions27:43 Understanding Debt vs. Equity Perspectives30:16 The Landscape of Self-Funded Search Deals33:30 Lessons from Real-World Acquisition Stories40:27 Resources for Self-Funded SearchersWhether you’re a first-time searcher or an investor learning the space, this episode is packed with tactical insight and real-world guidance.📩 Want to contact Lisa?https://www.linkedin.com/in/forrestlisa/📩 Want to contact or join SMB Investor Network?https://www.smbinvestornetwork.com/👉 Subscribe if you enjoyed this episode and for more interviews like this.💬 Leave your thoughts or questions in the comments