Investing in the Next Generation of Founders

April 28, 2025

Investing 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. For founders seeking hands-on guidance, I offer advisory services that go beyond capital to include strategic support, operational expertise, and network access.

My Investment Philosophy

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

Founder-Market Fit: Does the founding team have unique insights, experience, or advantages in their target market?
Problem Significance: Is the problem being solved substantial enough to create a large, sustainable business?
Execution Intelligence: Can this team adapt, learn, and execute effectively in a fast-changing environment?
Scale Potential: Does the business model allow for efficient scaling with favorable unit economics?
Values Alignment: Do the founders demonstrate integrity, resilience, and commitment to building responsibly?

Beyond Capital: The Support Entrepreneurs Really Need

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.

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.

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.

Regional Focus: Building Innovation Ecosystems

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. 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.

Current Investment Themes

My investment focus has evolved to concentrate on these key areas:

AI-Powered Enterprise Solutions: Applications that leverage artificial intelligence to solve specific business challenges
Healthcare Innovation: Technologies improving healthcare delivery, patient experience, and clinical outcomes
Future of Work: Tools and platforms that enable distributed teams to collaborate effectively
Sustainability Tech: Solutions addressing environmental challenges through innovative business models

For Founders Seeking Investment

If you're building something in these spaces and seeking investment, here's my advice:

Demonstrate Traction: Show evidence that your solution addresses a real need people will pay for
Know Your Numbers: Understand your unit economics, CAC, LTV, and path to profitability
Build Relationships Early: Connect before you need funding to establish rapport and understanding
Be Coachable: Show you can absorb feedback while maintaining your vision and conviction

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.

The Venture Studio Model - How Scalable Ventures builds and supports companies
Startup Playbook: From Idea to Product-Market Fit - Early-stage guidance for founders
B2B SaaS Scaling Playbook - Scale from $1M to $10M ARR
The Midwest Advantage - Why we invest in regional markets

Next Steps

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

Explore the portfolio: See companies we've built and invested in
Download resources: Access frameworks and templates I use with portfolio companies
Get in touch: Reach out to discuss potential collaboration

Explore More

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Investing in the Next Generation of Founders