Founder City | Session 10 – CEO Roundtable
In this session, one of Vistage’s top executive coaches, Ed Robinson, brings together a panel of successful Maryland-based CEOs to share their experiences as founders and valuable lessons learned.
Watch the full session here, then explore other Founder City content.
Panelists
- Ed Robinson – President, Capacity Building Solutions & Master Chair, Vistage International. Author of Reflections on Life and Leading, and On Business and Leadership
- Noah Berk – Co-founder & Strategy, obo. Agency
- Yair Flicker – President, SmartLogic
- Vlad Friedman – CTO, Databank Ltd. & CEO, Edge Hosting
- Jason Peay – CEO, VersaTech
- James Allen Schultz – President and Co-founder, R2Net LLC
- Robert Wray – Founder and CPO, Whitebox Inc
Highlights and Lessons Learned
Vlad Friedman – CTO, Databank Ltd. & CEO, Edge Hosting
Started a tech company at 18 in his parents’ basement. Scaled to 100 employees and $20M in revenue. Acquired by a private equity firm in 2017 and now CTO of a company with 64 data centers.
Lessons learned:
- Don’t be afraid to make mistakes or change course.
- Set clear expectations for roles early, especially with family.
Jason Peay—President/CEO, VersaTech
Launched a government IT firm out of grad school. Works with the FDA and Department of Transportation on public safety systems.
Lesson learned: Anything is possible with time and effort.
James Allen Schultz—President and Co-founder, R2Net LLC
Started JamesAllen.com with $5K. After 20 years, it was sold for $328M.
Lessons learned:
- Your 3-year plan may take 20 years—keep executing.
- Whatever success you envision, aim higher.
Noah Berk—Co-founder, obo. Agency
Tech consultancy helping businesses align tech stacks across departments. Emphasizes partnership clarity.
Lesson learned: Vet your business partner. Align around mission and values.
Yair Flicker—President/Founder, SmartLogic
Custom web/software app development. Fully virtual with 19 employees.
Lesson learned: It’s a marathon, not a sprint. Grow steadily.
Robert Wray—Founder and CPO, Whitebox Inc
Started multiple companies. Turned failure into success by building great software and growing a company that helps brands sell and ship products.
Lessons learned:
- Share your ideas and get feedback.
- Outside capital = change in control.
- Success attracts top talent.
Funding Insights
On Self-Funding
- Yair: Consulting businesses grow linearly. Self-funding maintains control but slows growth.
- Jason: Strategic decision to grow through contracts. Investment would now help with acquisition and scaling.
On Outside Investment
- James: Raised $150M and exited successfully. Risky but life-changing.
- Rob: Taking capital was about accelerating growth and working with smart people.
Lesson learned: Consider your risk tolerance and how much control you’re willing to give up. Outside investment is a trade-off that can open doors to growth and talent acquisition.
Final Thoughts
- Establish clear boundaries and roles, especially in family businesses.
- Put legal agreements in place, even with friends.
- Don’t try to do it all—hire a strong team.
- Outside capital can accelerate your journey, but it comes with strings attached.
Continue the conversation and watch the full session at FounderCity.com.
Vistage is the world’s largest executive coaching organization for small and midsize businesses. For 60+ years, it has helped leaders overcome their toughest challenges through powerful peer advisory groups and expert coaching.
