Building a valuable company isn’t simply about generating more revenue. It’s about learning from failure, protecting cash flow, creating repeatable systems, building the right team, and eventually deciding what you want your business to give you beyond money.

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with Kyle Ewing, chairman of Windward Equity and founder of TerraSlate, about Kyle’s evolution from entrepreneur to investor and chairman.

Kyle’s entrepreneurial journey included Guerrilla Tags ID Systems, an athlete identification product business, followed by Teslyne, a Tesla-based luxury transportation company. Neither journey was effortless. Guerrilla Tags taught him the difficulty of scaling a durable product without repeat purchases. Teslyne exposed the challenges of underpricing, capital-intensive growth, and operating a service business around the clock.

Those experiences became inputs for his next company, TerraSlate, which manufactures waterproof paper. One lesson became particularly important: get paid first. TerraSlate requires customers to prepay while purchasing raw materials on vendor terms. Kyle argues that this approach reduces collections headaches, improves cash flow, and helps a company fund its own growth—even when selling B2B to large organizations accustomed to 30-, 60-, or 90-day payment terms.

Kyle also explains why listening closely to customers can reshape a company’s growth strategy. TerraSlate originally pursued government applications, but customer requests uncovered opportunities ranging from restaurant menus and military applications to schools, retail environments, artists, and crafts.

Now, as an investor through Windward Equity, Kyle looks beyond financial statements. He values founders with a growth mindset, strong company culture, and a willingness to test ideas, learn, and execute. He also discusses the Rule of 40 as a framework for balancing growth and profitability, while emphasizing his preference for maintaining a profitability floor.

The conversation ultimately moves beyond valuation and M&A to something founders often overlook: time.

After years of entrepreneurship, Kyle has transitioned from TerraSlate’s full-time CEO into a chairman role. His goal today is to structure his businesses around the life he wants rather than structuring his life around his businesses. For founder-CEOs considering a business exit strategy, that may be one of the most important questions of all: What do you actually want your time to look like when the business no longer needs you?

Key Takeaways:

• Get paid upfront whenever possible and use vendor terms to strengthen cash flow and self-fund growth.
• Build recurring purchasing behavior; constantly acquiring one-time customers makes scalable growth significantly harder.
• Go where your customers already are and use direct conversations to uncover product and market opportunities.
• Customer feedback can reveal more valuable markets than the original business strategy anticipated.
• Strong company culture and accountable, growth-minded people can become a meaningful competitive advantage.
• Balance profitability and growth rather than pursuing revenue at any cost; Kyle uses the Rule of 40.
• Build repeatable operating systems so the company can perform without depending constantly on its founder.
• Exit planning should consider more than valuation—define what you ultimately want to do with your time.

Episode timestamps:

00:00 – Exit readiness assessment and episode introduction

00:55 – Meet Kyle Ewing: entrepreneur, investor, and chairman of Windward Equity

01:20 – Kyle’s entrepreneurial roots and education journey

03:05 – Leaving corporate life to become a full-time entrepreneur

05:10 – Ethics in business and recognizing how others operate

07:30 – Building GorillaTags from scratch and grinding for every sale

10:10 – Three costly scaling mistakes: operations, pricing, and capital requirements

14:05 – Using direct customer feedback to improve products and generate repeat sales

18:20 – How failure compounds entrepreneurial knowledge and improves future decisions

20:30 – Why Kyle requires customers to prepay

22:05 – Getting Fortune 500 customers to accept upfront payment terms

23:35 – Building TerraSlate’s waterproof paper technology

25:05 – How restaurant customers helped unlock TerraSlate’s growth

25:30 – Discovering unexpected customer segments and new use cases

27:30 – Moving from full-time CEO to chairman of TerraSlate

28:35 – Investing in businesses through Windward Equity

30:30 – What makes a business attractive to an investor or buyer

32:40 – Growth mindset versus fixed mindset when evaluating founders

35:25 – Kyle’s 13% net-income floor and approach to sustainable growth

36:25 – How founders can think about the right time to exit

39:00 – The danger of continually postponing a business exit

41:00 – Working on the business instead of staying trapped inside it

42:15 – Where to connect with Kyle and access his founder resources

42:55 – Bootstrapped to $40 Million and building a repeatable scaling system

Links & Resources:

• Kyle Ewing
  • Website: kyleewing.com
  • LinkedIn: www.linkedin.com/in/kyleewing/
  • Companies/Projects mentioned: Windward Equity, TerraSlate, Big Island Honey Company
    Resource mentioned: Bootstrapped to $40 Million

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