The SMB Investor

What happens when buying a business means putting your personal assets on the line?

In this interview, Sean Smith, Managing Partner of Search Fund Ventures and Founder of SMB Investor Network, sits down with Jason Hunt, Founder of Ink Insurance, to discuss personal guarantee insurance and the role it could play for entrepreneurs acquiring businesses with SBA financing.

The conversation examines whether a traditional personal guarantee encourages responsible ownership—or whether, in a distressed situation, the fear of losing everything can actually push an operator toward decisions focused primarily on protecting their own assets rather than maximizing value for lenders, investors, and the business.

The discussion also covers:

• How personal guarantee insurance works for SBA-backed business acquisitions
  • Why personal guarantees can be particularly significant for mid-career self-funded searchers
  • What happens to business and personal assets following a loan default
  • How Inc. Insurance evaluates businesses, buyers, and deal characteristics
  • Why coverage may vary depending on the assets inside the acquired business
  • Asset-light businesses versus companies with inventory, equipment or real estate
  • The potential impact of PG insurance on lenders and investors
  • Incentive alignment when a business enters financial distress
  • Why fear of personal financial loss can influence an operator’s decisions
  • How much personal risk an entrepreneur should retain
  • The types of searchers and acquisitions showing interest in the product
  • Potential applications for sellers rolling equity
  • Using personal guarantee insurance in a second acquisition
  • Thinking about the downside case—not just growth and exit scenarios—before acquiring a business

If you're a self-funded searcher, entrepreneur, investor, lender, or considering buying a business using SBA financing, this conversation offers a detailed look at an often overlooked part of acquisition risk: the personal guarantee.

Subscribe for more conversations on search funds, entrepreneurship through acquisition, SBA financing, and buying and operating small businesses.

What do you think: does personal guarantee insurance improve incentive alignment for business buyers, or could it encourage greater risk-taking? Leave your thoughts in the comments.

Connect with the speakers:

• Ink Insurance Website & Application: https://inkinsurance.com/
• Jason Hunt LinkedIn: https://www.linkedin.com/in/jasonchrishunt/
• Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/

In this episode, Sean Smith sits down with Dylan Gans, founder of Baton, to discuss how technology is transforming the way small businesses are bought and sold.

Drawing from his entrepreneurial background and experience selling a startup to Aramark, Dylan shares why he believes millions of small businesses need better succession solutions and how Baton is modernizing the traditionally fragmented business brokerage industry.

The conversation explores why relationships matter more than ever in acquisitions, how buyers can improve their chances of closing deals, why many owners have unrealistic expectations about valuation, and how Baton combines technology with experienced M&A advisors to simplify the entire transaction process.

Sean and Dylan also discuss:

Why millions of small businesses will change hands over the next decade
The "Silver Tsunami" creating unprecedented acquisition opportunities
Common mistakes first-time buyers make
Why passive ownership is often an unrealistic expectation
Building trust between buyers and sellers
Off-market opportunities and Baton's valuation-first approach
How AI is changing white-collar work—and why entrepreneurship may become even more important
Lessons learned from hundreds of small business transactions

00:00 Introduction to Innovative Brokerage Solutions
01:13 Dylan Gans' Entrepreneurial Journey
04:22 Bridging Technology with Traditional Brokerage
10:03 Understanding the Value of Business Valuation
15:14 Enhancing Buyer-Seller Relationships
19:44 Exploring Off-Market Deal Dynamics
22:40 Understanding Seller Expectations
27:20 Building Trust in Buyer-Seller Relationships
29:52 Common Buyer Pitfalls
37:12 Real-Life Examples of Thoughtful Engagement
41:44 The Call to Action for Future Buyers

Whether you're an entrepreneur, search fund operator, acquisition entrepreneur, investor, or simply interested in buying your first business, this conversation offers valuable insights into today's SMB acquisition landscape.

If you enjoyed this interview, be sure to subscribe for more conversations with entrepreneurs, investors, and operators shaping the future of small business acquisitions.

📩 Connect with the speakers:

• Dylan Gans: https://www.linkedin.com/in/dylan-gans/
• Baton: https://www. baton.com
• Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/

Leave your thoughts or questions in the comments—we'd love to hear your perspective.

How do you go from running a family-owned home healthcare agency to building a technology-enabled acquisition platform?

In this episode, Sean Smith, Managing Partner at Search Fund Ventures and Founder of SMB Investor Network, sits down with Karl Pierre, Founder of Aidbook Holdings, to discuss his unique journey from helping grow his family's healthcare business to over $10 million in annual revenue to launching a roll-up strategy focused on acquiring home healthcare agencies.

Karl shares how conversations with private equity buyers completely changed the way he viewed business growth and valuation. Instead of selling, he decided to build his own acquisition platform—leveraging industry expertise, proprietary software, and strategic acquisitions to create long-term value.

In this conversation, you'll learn:

00:00 The Journey Begins: From Family Business to Tech-Enabled Growth
05:13 Acquisition Strategy: Growing Through Consolidation
10:39 Tech Enablement: Building Solutions for the Future
16:11 Deal-Making Insights: Cash is King
21:26 Navigating Challenges: Lessons from Failed Deals
26:37 The Future of Home Care: Opportunities Ahead

Whether you're an SMB investor, searcher, healthcare entrepreneur, or acquisition entrepreneur, this episode offers practical insights into building value through acquisitions and technology.

If you enjoyed this conversation, subscribe for more interviews with experienced operators, investors, and acquisition entrepreneurs.

Leave your thoughts or questions in the comments—we'd love to hear your perspective.

📩 Connect with the speakers:

• Karl Pierre LinkedIn: https://www.linkedin.com/in/karl-pierre-63028052/
• Aaidebook: https://www.aaidebook.com/
• Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/

Anthony Macleod shares his journey from entrepreneur to Pinnacle Business Guide, emphasizing the transformative power of business operating systems like EOS and Pinnacle. Discover how implementing these systems can drive focus, improve team alignment, and significantly increase enterprise value.

Tivan Amour shares his journey from being a serial entrepreneur to working with ETA (Entrepreneurship Through Acquisition) entrepreneurs. He discusses the importance of grit, patience, and the right mindset in entrepreneurship, as well as the transferable skills from startups to ETA. Tivan emphasizes the significance of sales strategies, experimentation, and building effective sales teams. He also provides insights for investors on assessing sales and growth potential in ETA entrepreneurs and the importance of systems in driving growth.

In this conversation, Lisa Piercey shares her journey from being a physician to becoming a successful business buyer in the healthcare sector. She emphasizes the importance of industry experience in making successful acquisitions and building trust with stakeholders. Lisa discusses her approach to evaluating potential investments, structuring deals, and mitigating risks. She also highlights the emotional aspects of business buying and offers insights from her book, 'Natural Born Entrepreneurs,' which serves as a guide for mid-career professionals considering entrepreneurship through acquisition.

In this in-depth conversation, Sean Smith, Managing Partner of Search Fund Ventures and Founder of SMB Investor Network, sits down with Jon Staenberg, Founder & CEO of Agate Hound Fund, to explore the evolution of search funds and the rise of microcap private equity.

Jon shares firsthand perspective from the earliest days of search at Stanford Business School, how the traditional search fund model emerged, and why he views it as microcap private equity with a repeatable playbook. The discussion covers portfolio-style investing through a fund-of-funds approach, diversification and access for investors, and how demographic tailwinds are shaping the future of small business acquisitions.

They also examine how the search ecosystem is evolving, differences between traditional MBA-led search and mid-career operators, and why technology and AI may meaningfully improve acquisition diligence, operating efficiency, and long-term outcomes in SMBs.

This episode is essential viewing for investors, operators, and anyone interested in entrepreneurship through acquisition and long-term value creation in the SMB market.

👉 Subscribe for more long-form interviews on SMB investing and acquisition strategies.💬 Share your thoughts or questions in the comments below.

📩 Connect with the speakers:

• Jon Staenberg LinkedIn: https://www.linkedin.com/in/jonstaenberg/
• Jon Staenberg Email: [email protected]
• Agate Hound Fund: https://www.aggathound.fund
• Sean Smith 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 and Founder of SMB Investor Network, sits down with Michael Huseby, founder of The Investment Lawyers, to break down the real-world legal dynamics behind LP agreements, fund structures, 506(c) fundraising, governance rights, waterfalls, fund expenses, and minority protections.

Michael shares insights from his work across private equity, SMB acquisitions, real estate, private credit, venture capital, and SPV formation—explaining what LPs should look for, how GPs are negotiating deals today, and why trends are shifting toward cash-flow strategies.

Topics covered include:

• Why Michael left Big Law to start his own firm
• His new book Fundamentals and why he “shares the sauce”
• LP trends: cash-flowing strategies, anchor investors, and GP-stake asks
• The rise of 506(c) and recent SEC guidance on accreditation
• Governance: top protections LPs should check for in documents
• Fund expenses: what’s reasonable, what’s not
• Waterfall structures: simple to advanced, including GP catch-ups and dual waterfalls
• How LPs should evaluate liquidity, continuations, and risk
• Key pitfalls LPs commonly miss in documents
• Why clear marketing disclosures protect GPs from securities issues

Looking for an specific minute?

00:00 Introduction to Limited Partnerships and LP Agreements02:39 Transitioning from Big Law to Independent Practice05:33 Current Trends in Investment Strategies08:19 Understanding GP Stakes and Investor Influence10:59 The Shift to 506C and Public Fundraising13:25 Governance and Minority Protections in Investment Documents16:28 Key Considerations for Limited Partners19:09 Liquidity and Fund Structures21:35 Understanding Fund Expenses24:41 Waterfall Structures in Fund Distributions36:15 Conclusion and Resources for Further Learning

If you're an investor, operator, or GP raising capital, this episode delivers a practical, plain-English deep dive from one of the most active fund attorneys in the SMB and alternatives ecosystem.

👉🏻 Subscribe for more interviews like this and share your thoughts in the comments.

📩 Connect with the speakers:

• Michael Huseby – The Investment Lawyers: https://www.til.law/
• Michael Huseby LinkedIn: https://www.linkedin.com/in/michael-bjorn-huseby/
• Fundamentals Newsletter: https://www.til.law/#newsletter
• 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 of Search Fund Ventures and Founder of SMB Investor Network, sits down with Ariez Dustoor of NB Group, an experienced independent sponsor with meaningful reps investing in both sponsors and searchers.

Ariez shares a rare dual-sided view of the market—how he evaluates deals, how his sector focus evolved, how he builds pattern recognition, and what true discipline looks like in dealmaking. He breaks down the challenges of sourcing, negotiating, and closing transactions, the realities of post-close execution, and what he looks for in leadership teams.

Key themes include:

• Sector specialization in healthcare and multi-location services
• Maintaining discipline through cycles without committed capital
• Creative deal structuring and managing “near-death” transactions
• Pattern recognition and narrowing the investment strike zone
• Post-close leadership evaluation, strategic planning & professionalization
• How independent sponsors differ from committed funds
• Capital raising process, working with placement agents, and LP alignment

⚡️ If you’re a searcher, operator, LP, or independent sponsor, this conversation is packed with real-world lessons directly from the trenches.

** Subscribe for more conversations like this, and leave your thoughts or questions in the comments.

📩 Connect with the speakers:

• Ariez Dustoor LinkedIn: https://www.linkedin.com/in/ariezdustoor/
• NB Group Website: http://www.nbgroup.us
• Sean Smith LinkedIn: https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/

In this interview, Sean Smith, Managing Partner of Search Fund Ventures and Founder of the SMB Investor Network, sits down with Robert Graham, Co-Founder of SIG Partners and Co-Founder of Pillar Health Group.

Robert shares his journey from HBS to building a healthcare group that grew from $6M in revenue to $130M+, powered by both organic growth and acquisitions.

Together, Sean and Robert unpack:

• The evolution of self-funded search and the role of SBA financing.
• A new SBA policy that could permanently ban investors with prior 7A loan defaults — and its ripple effects on entrepreneurs, lenders, and small business owners.
• Investor diligence: debt service coverage, leverage, IRR vs. MOIC, and why “step-ups” can be misleading.
• Industry heuristics: how to think about recurring revenue, installation, and construction risk in trades and building services businesses.
• What investors should consider when evaluating cost of capital, revenue buckets, and risk-adjusted returns.

This conversation highlights both the opportunities and challenges ahead for searchers, operators, and investors in the SMB ecosystem.

👉 Subscribe for more interviews with leading investors and operators in SMBs.

💬 Share your thoughts in the comments — how do you see SBA changes impacting the space?

Connect with the speakers:

• Robert Graham (LinkedIn): https://www.linkedin.com/in/robertelliotgraham/
• SIG Partners: sigpartners.com
• Pillar Health Group: https://www.pillarhealthgroup.com/
• Sean Smith (LinkedIn): https://www.linkedin.com/in/sean-smith-47ab2a70/
• SMB Investor Network: https://www.smbinvestornetwork.com/