About
Media
Startups & Experiments
Advisory
Writing
Resources
Contact
Posts

Investing in the Next Generation of Founders

April 28, 2025
Investing in the Next Generation of Founders

Why Do I Invest in the Next Generation of Founders?

First-hand Experience
Active investor through Scalable Ventures, Unbridled Ventures, and Poplar Ventures(Invested in and advised 50+ startups with multiple successful exits)
After founding and scaling multiple successful companies, including UnifyCX and participating in Backupify's growth journey to acquisition, I've shifted significant focus to investing in and mentoring the next generation of entrepreneurs. Through Scalable Ventures, I've had the privilege of working with dozens of founders at various stages of their entrepreneurial journey. The truth is, I invest because I remember what it was like to build something from nothing. When I co-founded UnifyCX, there was no playbook for scaling a customer experience company to over 6,000 employees. We figured it out through trial and error, long nights, and a handful of advisors who had walked the path before us. That experience shaped how I think about founder support today. The best investors I encountered did not just write checks — they rolled up their sleeves and helped me solve problems I had never seen before. That is the kind of investor I aspire to be. Every founder I back reminds me of a version of myself at different stages: the first-time founder with a brilliant technical insight but no go-to-market strategy, the repeat entrepreneur who underestimates how different the second company will be, or the domain expert who sees a massive opportunity but needs help translating it into a scalable business. These are the moments where operational experience matters more than capital, and where the right guidance can compress years of learning into months. For founders seeking hands-on guidance, I offer advisory services that go beyond capital to include strategic support, operational expertise, and network access.

What Do I Look For When Investing in Startups?

When evaluating potential investments, I look beyond just the business metrics to understand:
Investment Criteria
1
Founder-Market Fit
Unique insights and advantages in target market
2
Problem Significance
Large enough to build a sustainable business
3
Execution Intelligence
Ability to adapt, learn, and execute
4
Scale Potential
Efficient scaling with favorable unit economics
5
Values Alignment
Integrity, resilience, responsible building
These five pillars form the foundation of every investment decision I make. Founder-market fit tells me whether the team has a genuine, hard-to-replicate advantage in their space. Problem significance ensures we are not optimizing around a trivial pain point. Execution intelligence separates the founders who can adapt from those who freeze when the plan falls apart. Scale potential reveals whether the business model can grow efficiently without burning through capital. And values alignment — often the most underrated — determines whether I can trust this team through the inevitable hard stretches. I have passed on deals with strong metrics because the founder's values did not align with how I believe companies should be built, and I have never regretted those decisions.
  1. Founder-Market Fit: Does the founding team have unique insights, experience, or advantages in their target market? I look for founders who have lived the problem they are solving. When I evaluated an investment in a healthcare technology company, the founder had spent a decade as a hospital administrator and understood the procurement cycle, the regulatory constraints, and the clinical workflows in a way that no outsider could replicate. That kind of embedded knowledge is a competitive moat that no amount of funding can buy. Conversely, I have seen brilliant technologists build solutions for markets they did not understand, and those ventures almost always stall once they hit the complexity of real customer needs.
  2. Problem Significance: Is the problem being solved substantial enough to create a large, sustainable business? I want founders who are tackling problems where the customer's pain is acute and measurable. If a prospect cannot articulate the cost of the status quo in dollars, hours, or risk, the problem may not be significant enough. At Backupify, we addressed the very real fear of cloud data loss at a time when enterprises were migrating to SaaS platforms without backup strategies. The urgency of that problem drove rapid adoption. I look for that same urgency in every pitch.
  3. Execution Intelligence: Can this team adapt, learn, and execute effectively in a fast-changing environment? I pay close attention to how founders respond when I challenge their assumptions during the diligence process. The best founders do not get defensive — they get curious. They ask follow-up questions, they update their thinking, and they come back with a revised approach. I have watched portfolio companies pivot their entire go-to-market strategy in a matter of weeks because the founders had the intellectual humility to recognize what was not working and the speed to act on it.
  4. Scale Potential: Does the business model allow for efficient scaling with favorable unit economics? I have seen too many startups grow revenue while destroying value because their unit economics never worked. I look for businesses where the cost to acquire a customer decreases over time, where gross margins improve with scale, and where there is a natural expansion path within existing accounts. When I helped scale UnifyCX, we learned that operational efficiency at scale was not automatic — it required deliberate systems thinking around hiring, training, and quality assurance. I bring that same lens to evaluating whether a startup's model can actually scale.
  5. Values Alignment: Do the founders demonstrate integrity, resilience, and commitment to building responsibly? This is non-negotiable for me. I want to work with founders who treat their employees well, who are transparent with their investors, and who build products that genuinely serve their customers. I have walked away from high-return opportunities when I sensed that the founder's primary motivation was personal enrichment rather than value creation. The companies I am most proud to be associated with are the ones that built something meaningful — not just profitable.

What Support Do Entrepreneurs Really Need Beyond Capital?

Throughout my years of investing, I've found that capital alone rarely determines startup success. The most impactful support often comes in other forms:

Strategic Guidance

Many founders excel in their domain expertise but need guidance navigating strategic decisions about market positioning, pricing, or go-to-market strategies. I provide regular strategic reviews with portfolio companies, helping them see around corners and make informed decisions. One pattern I see repeatedly is founders underpricing their product because they fear losing deals. I worked with a B2B SaaS company in our portfolio that was charging a fraction of what the market would bear. After we conducted a pricing analysis together — mapping their value delivery against competitive alternatives — they raised prices by 40% and saw virtually no churn. That single change improved their runway by over a year. Strategic guidance like this is not glamorous, but it can be the difference between running out of cash and reaching profitability.

Network Access

One of the most valuable resources I offer is connections to potential customers, partners, advisors, and future investors. My network across the tech, SaaS, and AI landscapes has been built over decades and spans from startups to enterprise organizations. Warm introductions are the currency of early-stage growth. Through my involvement with Unbridled Ventures, Poplar Ventures, and Venture First, I can connect founders not just to potential customers but to other investors for follow-on rounds, to experienced operators who have scaled similar companies, and to strategic partners who can accelerate distribution. I have seen a single well-timed introduction turn a stalled sales pipeline into a company's largest contract.

Operational Expertise

Having scaled companies to thousands of employees, I've developed frameworks for navigating the operational challenges of growth. I help founders build scalable systems for recruitment, team structure, culture development, and process optimization. The operational challenges change dramatically at each stage. What works with a team of 10 breaks at 50, and what works at 50 breaks at 200. At UnifyCX, we went through every one of those transitions and learned hard lessons about when to centralize versus decentralize decision-making, how to maintain culture as you add hundreds of people per year, and when to invest in process versus when to stay scrappy. I share these frameworks with portfolio companies so they can avoid the mistakes that cost us time and money.

How Can Regional Markets Drive Innovation?

While I invest nationally, I maintain a special focus on building and strengthening the entrepreneurial ecosystem in Kentucky and the broader Midwest region. These markets often have exceptional talent and unique advantages but historically less access to venture capital and startup resources. I have seen firsthand what happens when talented founders in regional markets get the same access to capital, mentorship, and networks that their counterparts in San Francisco or New York take for granted. The cost advantages are real — lower salaries, lower rent, lower customer acquisition costs in certain verticals — but the bigger advantage is focus. Founders outside the coastal bubble are less distracted by hype cycles and more focused on building sustainable businesses that solve real problems for real customers. Through local initiatives, mentorship programs, and strategic investments, I'm working to create self-sustaining innovation hubs that can generate and support multiple generations of successful companies. The goal is not to replicate Silicon Valley but to build something better suited to the strengths of these communities: deep industry expertise in healthcare, logistics, manufacturing, and agriculture, combined with a pragmatic approach to company building that prioritizes profitability alongside growth.

What Are the Investment Themes I Am Most Excited About?

My investment focus has evolved to concentrate on these key areas:
  1. AI-Powered Enterprise Solutions: Applications that leverage artificial intelligence to solve specific business challenges. I am especially interested in vertical AI — purpose-built models that serve a specific industry or function rather than horizontal platforms. The companies that will win in AI are not building general-purpose tools; they are embedding intelligence into workflows where domain expertise creates defensibility. Through Scalable Ventures, we are building products like Revoyant and HiveDesk that embody this thesis.
  2. Healthcare Innovation: Technologies improving healthcare delivery, patient experience, and clinical outcomes. Healthcare is one of the largest and most inefficient sectors in the US economy, and the regulatory complexity creates natural barriers to entry that protect startups with the right domain expertise. I look for teams that understand both the clinical and business side of healthcare — companies like SentryHealth in our portfolio that sit at that intersection.
  3. Future of Work: Tools and platforms that enable distributed teams to collaborate effectively. The shift to remote and hybrid work is permanent, and the tooling has not caught up. I am particularly interested in companies that address the management and culture challenges of distributed teams, not just the communication layer.
  4. Sustainability Tech: Solutions addressing environmental challenges through innovative business models. This is a space where real business value and social impact can align, and I believe the next decade will produce several category-defining companies in energy, waste reduction, and supply chain sustainability.

What Advice Would I Give Founders Seeking Investment?

If you're building something in these spaces and seeking investment, here's my advice:
  1. Demonstrate Traction: Show evidence that your solution addresses a real need people will pay for. Traction does not always mean revenue — it can be letters of intent, pilot results, or a waitlist that demonstrates genuine demand. But you need to show me that you have moved beyond the idea stage and validated your assumptions with real customers. The strongest signal I see is a founder who can name their first 10 customers and explain why each one bought.
  2. Know Your Numbers: Understand your unit economics, CAC, LTV, and path to profitability. I am surprised by how many founders at the seed stage cannot articulate their gross margin or explain how their customer acquisition cost will evolve as they scale. You do not need perfect answers, but you need to demonstrate that you are thinking rigorously about the economics of your business, not just the product.
  3. Build Relationships Early: Connect before you need funding to establish rapport and understanding. The best investment decisions I have made were with founders I knew for months or years before writing a check. When you reach out only when you need money, you are asking someone to make a high-stakes decision with limited information. Start the conversation early, share your progress, and let potential investors watch you execute over time.
  4. Be Coachable: Show you can absorb feedback while maintaining your vision and conviction. There is a difference between being coachable and being a pushover. I want founders who listen carefully, consider new information, and then make their own decision — even if it differs from my advice. The founders who simply agree with everything an investor says are just as concerning as the ones who dismiss every suggestion.
The journey from founder to investor has taught me that successful entrepreneurship is a team sport. While founders must drive vision and execution, surrounding yourself with the right supporters, advisors, and investors can make the difference between success and failure in building a transformative company.

Related Reading

Next Steps

If you're building in AI, SaaS, healthcare, or sustainability and seeking investment or strategic guidance:

Related Articles

Explore more insights on entrepreneurship, AI, and leadership:

Explore More

Dive deeper into related topics and resources:
On this page