From Angel To Exit

From Angel To Exit is a business podcast exploring the entrepreneurial journey of scaling a business from raising your first round of funding to exiting. We cover the trials and tribulations that founders face, the pitfalls and pratfalls you want to avoid, as well as the joy and impact that success can bring. Join us on our next episode, where we speak about the challenges that real leaders face growing and scaling their organizations and how they’ve overcome them to achieve success and make their mark.

From Angel To Exit is a business podcast hosted by Bruce Eckfeldt, with 59 episodes on record and a Required Pod Score of 80.

Bruce Eckfeldt hosts From Angel To Exit, a business show with 59 episodes published.

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  Episode #58

  58: From Founder Dependence to Freedom: How to Build a Business That Thrives Without You

  Sep 23, 202644 min

  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 Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

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  Episode #57

  57: Worried About Your Exit? How to Use ESOP to Create Liquidity, Tax Benefits, and Employee Wealth

  Sep 2, 202643 min

  What if you could take significant money off the table without immediately selling your entire company to private equity or a strategic buyer? In this episode of From Angel to Exit, Bruce Eckfeldt speaks with Larry Kaplan, Managing Director at CSG Partners, about Employee Stock Ownership Plans (ESOPs) and why founder-CEOs should consider them when evaluating their business exit strategy. Larry describes an ESOP as essentially a leveraged buyout of your own company. A trust is established on behalf of employees, financing is raised against the company, and the ESOP uses those funds to acquire shares from the owner. Unlike a traditional M&A transaction, the buyer is ultimately a trust operating for the benefit of employees. That structure can create compelling benefits. Larry explains the potential capital-gains tax deferral available under certain ESOP structures, corporate tax deductions, and the powerful tax treatment available to qualifying 100% ESOP-owned S corporations. These advantages can increase free cash flow and help companies repay transaction debt more quickly. ESOPs also provide flexibility in succession and exit planning. Owners don’t necessarily have to sell 100% immediately. A founder might begin by selling 30% to 49%, creating liquidity while maintaining independence and leadership. An employee-owned business can execute additional transactions as the company reduces its debt and the founder progresses toward a full exit. The episode also examines where ESOPs fit relative to private equity and strategic acquisitions. ESOPs generally cannot compete on sale price alone if a strategic buyer willing to pay a substantial premium because of unique synergies. But for founders concerned about preserving jobs, company culture, community impact, and legacy, employee ownership can offer advantages beyond headline valuation. Larry also stresses that ESOPs aren’t risk-free. Companies need profitability, positive cash flow, and strong future prospects. Excessive leverage can create problems just as it can in any leveraged acquisition. For founders preparing for an eventual sale, the message is straightforward: evaluate ESOPs alongside traditional M&A options. Understanding the after-tax economics, financing, valuation, succession needs, and long-term outcomes can reveal an exit strategy many business owners never realize is available. Key Takeaways: An ESOP can provide founder liquidity without requiring an immediate 100% sale of the business. ESOP transactions can offer significant tax advantages that materially change the after-tax economics of an exit. Founders can use staged ESOP transactions to combine liquidity today with a longer-term succession plan. Strong ESOP candidates are typically profitable businesses with stable cash flow and good long-term prospects. Over-leveraging the company is one of the biggest risks when structuring an ESOP transaction. ESOPs can preserve jobs, culture, community presence, and founder legacy while creating employee ownership. Strategic buyers may pay higher premiums, making ESOPs one option to compare within a broader M&A strategy. Founders should compare ESOP and private equity outcomes over five- and ten-year horizons, not just headline valuation. Episode Timestamps: 00:00 Exit Planning Resources 00:50 Meet Larry Kaplan 01:32 Larry’s ESOP Origin Story 04:41 ESOP History and Purpose 08:13 How ESOPs Work 09:29 Tax Benefits Explained 12:24 Why Government Supports ESOPs 14:42 Employee Role and Risk 16:31 Best Fits and Deal Size 18:50 Control and Full Exit Options 21:31 Financing and Managing ESOP Debt 22:10 Debt and Covenants 23:10 When ESOPs Go Wrong 24:47 Employee Vesting and Payouts 26:00 ESOP Versus PE Or Strategic 28:55 How Fair Market Value Is Set 31:34 Deal Terms and Defaults 33:50 Fees and Banker Incentives 35:41 Evaluating an ESOP Option 37:22 Market Growth and Trends 40:09 Legislation and Future Outlook 42:02 Contact Info and Wrap Up Links & Resources: Larry Kaplan Email: lkaplan@csgpartners.com Website: csgpartners.com Office: 212.385.1375 Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

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  Episode #56

  56: Exit Planning Starts Early: Strengthen Financials and Leadership to Maximize Business Valuation - Dan Bauer

  Aug 26, 202641 min

  What makes a business valuable to a buyer—and what decisions can quietly make an eventual exit harder? Dan Bauer brings a unique perspective to that question. After growing up in his parents’ HVAC business, building a corporate marketing career that included Bank of Hawaii, Citibank, and MasterCard, and earning his MBA from Harvard Business School, Dan made the leap into entrepreneurship. He eventually built The MBA Exchange into a global advisory company with roughly 80 advisors, multiple service lines, and significantly less dependence on himself as founder. Those scaling decisions became especially important when Dan began considering an exit. Rather than simply growing revenue, he had created a broader management team, diversified the business, expanded internationally, and developed complementary offerings—all characteristics that helped make the company more saleable. Dan shares what happened when he initially took the business to market through an intermediary. Conversations with potential buyers became more financial than strategic, creating a mismatch with his desire to protect the brand and legacy he had spent two decades building. He ultimately sold the company to an insider who understood the business. The experience produced valuable lessons for founder-CEOs considering their own business exit strategy. Dan discusses the complexities of finding the right M&A advisors, negotiating an LOI, handling attempts to renegotiate terms, and surviving a surprisingly demanding due diligence process. He also explains the transaction structure, which included significant cash at closing, a two-year consulting arrangement, and seller financing. For founders preparing for an eventual sale, Dan recommends thinking seriously about exit readiness around two years before going to market. That creates time to produce multiple years of credible financial performance, improve margins, tighten financial reporting, strengthen leadership, and prepare employees for a transition. He also warns against decisions that can constrain future value—including overly founder-centric branding, narrowly naming a company around its current offering, unnecessary partnerships, and building everything internally. Strategic alliances, he argues, can provide credibility, capabilities, distribution, and scale while making a company more attractive to potential buyers. The central lesson: build your company today in a way that gives you more options when it is eventually time to exit. Key Takeaways: Start serious exit planning roughly two years before a sale to establish credible financial and growth trends. Reduce founder dependence by developing trusted leaders who can successfully operate the company after your departure. Tight, accessible financial records can make due diligence faster and reduce friction during an M&A transaction. Avoid company names that depend heavily on the founder or restrict future expansion into adjacent markets. Strategic alliances can accelerate scale, increase credibility, open distribution channels, and strengthen business value. Evaluate strategic versus financial buyers based on your valuation goals, culture, employees, brand, and desired legacy. Treat an LOI as intent rather than certainty; important deal terms can still become points of negotiation. Structure your exit knowing deferred payments and earn-outs carry risk; prioritize sufficient value at closing. Episode Chapters: 00:00 — Exit readiness resources and episode introduction 00:55 — Meet Dan Bauer: entrepreneurship, business strategy, and exits 01:35 — Growing up inside a family-owned HVAC business 02:35 — From advertising to corporate marketing and Harvard Business School 04:45 — Leaving corporate life to become an entrepreneur 05:20 — The MBA Exchange’s first failure—and the pivot that changed everything 06:40 — Early entrepreneurial lessons: customer service, hard work, and profitability 08:00 — Building The MBA Exchange from a spare bedroom 09:20 — Scaling from founder-led advising to an 80-person team 10:50 — Expanding internationally and adding complementary business lines 12:15 — Building a more saleable business by reducing founder dependence 12:50 — When Dan first realized it was time to consider an exit 14:20 — Hiring an intermediary and searching for strategic buyers 16:00 — Why financially focused buyers weren’t the right fit 16:40 — An unexpected management buyout opportunity emerges 17:25 — Exit lessons: choosing advisors and maintaining negotiating leverage 18:40 — LOI negotiations and why “intent” doesn’t mean commitment 19:40 — The hidden workload of M&A due diligence 20:20 — Deal structure: cash at closing, consulting fees, and seller financing 21:20 — Life after selling: replacing the identity of being a founder 23:00 — Building an entrepreneurship program through strategic partnerships 24:20 — Why the Shark Tank partnership didn’t work—and the pivot to Inc. 26:20 — Mentoring founders and launching Post Game Careers 28:15 — Exit mistakes founders make before they even think about selling 28:35 — Why founder-centric and overly narrow business names can hurt growth 29:35 — The risks of choosing a business partner too early 30:30 — Using strategic alliances to increase scalability and business value 31:50 — Why exit planning should begin roughly two years before a sale 32:40 — Strengthening revenue, margins, market share, and financial records 33:30 — Building a leadership team that can operate without the founder 34:35 — Strategic buyers vs. financial buyers: understanding the difference 36:30 — Structuring an exit around cash flow, risk, and personal priorities 38:30 — Why founders should prioritize sufficient cash at closing 39:10 — The risk of earn-outs and deferred payments 39:30 — Where to connect with Dan Bauer and learn more about his work Links & Resources: Dan Bauer LinkedIn: https://www.linkedin.com/in/bauerdan/ Website: https://www.bauer-inc.com/ Exit advisory: https://exitwise.com/ Post-athlete career advisory: https://www.postgamecareers.com/m Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

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  Episode #55

  55: Can Your Revenue Scale? Five Questions That Strengthen Your Business Exit Strategy - Rick McPartlin

  Aug 19, 202642 min

  A potential buyer doesn’t just want to know how much revenue your company generates today. They want to understand where that revenue comes from, whether it’s repeatable, and—most importantly—how the business can generate significantly more of it after the transaction. In this episode of From Angel to Exit, Bruce Eckfeldt speaks with revenue science expert Rick McPartlin about building a revenue strategy that can support scalable growth and strengthen the story a founder tells during an exit process. Drawing on nearly four decades of experience, Rick explains how his fascination with revenue systems began when he discovered that operational inefficiencies were forcing him to stop selling simply to ensure closed deals were successfully delivered. That experience led to a bigger realization: revenue isn’t just a sales issue. It’s an organizational system. Rick estimates that the “cost of chaos” in B2B organizations can represent 20–40% of top-line revenue, with cross-silo conflict accounting for a significant portion. Sales, marketing, finance, product, and operations can each optimize their own KPIs while unintentionally making the overall company less effective. The solution begins with a clear revenue strategy. Rick identifies five essential questions leadership teams must answer: What is your brand promise? What unique customer problem do you solve? What niche will you dominate? Who is your ideal buyer? And what offer ties everything together in a compelling way? Bruce and Rick also examine what this means for founder-CEOs preparing for M&A or a business exit. A spreadsheet showing aggressive future growth isn’t enough. Buyers and private equity investors can dig into how leads are generated, whether the addressable market supports the forecast, how efficiently people generate revenue, and whether the existing growth engine can truly scale. The conversation ultimately challenges founders to move beyond tactical sales management and build a unified, adaptable revenue system. In a volatile environment, businesses need enough strategic structure to absorb unexpected changes without rebuilding their strategy from scratch. That resilience can create stronger customer trust, more predictable growth, and a more credible value-creation story for potential buyers. Key Takeaways: Revenue should be managed as a company-wide system, not simply delegated to the sales organization. Cross-functional conflict and operational friction can consume a substantial portion of potential top-line revenue. Define your brand promise, unique customer problem, niche, ideal buyer, and compelling offer before attempting to scale. Stop chasing any available revenue; prioritize consistent, scalable, profitable growth around your ideal customer. Customer conversations and frontline sales insights create critical feedback loops for improving your revenue strategy. Increasing headcount and capital doesn’t automatically create scalable growth; improving organizational capacity can be more powerful. Exit-ready founders need a credible growth story supported by market dynamics, revenue processes, and customer behavior. Build enough strategic structure that your company can adapt to disruption without abandoning its core revenue strategy. Episode Chapters: 00:00 — Exit readiness, valuation, and preparing for a successful transaction 00:53 — Introducing Rick McPartlin and the science of revenue 01:40 — How operational bottlenecks sparked Rick’s focus on revenue systems 04:43 — The hidden “cost of chaos” inside B2B companies 06:38 — Why leadership teams must think beyond departmental KPIs 09:32 — Building a revenue culture around customer value 11:45 — Why inconsistent sales approaches make scaling difficult 12:42 — The five questions behind a scalable revenue strategy 17:41 — Understanding what customers actually need and value 19:03 — “Brain vs. stuff”: identifying what your market is really buying 21:38 — Turning sales conversations into a customer-insight feedback loop 23:37 — Learning faster and making smarter revenue decisions amid uncertainty 26:15 — Building an adaptable strategy that can withstand disruption 27:16 — Why not all revenue creates the same value during an exit 28:36 — Scaling through capacity instead of simply adding capital and headcount 30:43 — Measuring revenue efficiency through talent and payroll investment 32:00 — Hiring for purpose, collaboration, and organizational performance 33:22 — How founders can build a credible revenue-growth story for private equity 34:37 — Why cutting marketing to boost EBITDA can undermine future growth 36:42 — The leadership mindset shift from sales tactics to revenue science 39:05 — Building a resilient revenue strategy for an unpredictable market 41:45 — Where to connect with Rick McPartlin Links & Resources: Rick McPartlin Website: The Revenue Game: https://www.therevenuegame.com/ Email: rick.mcpartlin@therevenuegame.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

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  Episode #54

  54: How Dream Water Created a New Consumer Category and Achieved a Successful Exit | David Lekach

  Aug 5, 202647 min

  What happens when a founder ignores conventional startup advice and simply focuses on solving problems better than anyone else? David Lekach grew up immersed in entrepreneurship, learning firsthand from his family's successful retail businesses before launching ventures of his own. His entrepreneurial journey eventually led him to discover an early natural sleep aid product that inspired the creation of Dream Water—a beverage designed to become the "anti-Red Bull." Rather than chasing lofty exit valuations or rigid business plans, David concentrated on consistently making better operational decisions. He discusses how launching first in New York through Duane Reade allowed the company to validate product-market fit while gathering the retail data necessary to expand into larger national chains like Walgreens, CVS, and Walmart. The conversation explores the realities behind building a completely new product category. David explains how competition emerged almost immediately, why category creation often requires competitors, and how founders must balance innovation with disciplined execution. Bruce and David also dive deeply into the less glamorous side of entrepreneurship, including fundraising, scaling retail distribution, cash flow management, legal battles, and surviving a multi-year class action lawsuit. Throughout each challenge, David emphasizes the importance of remaining resourceful, data-driven, and willing to question conventional wisdom. One of the episode's most valuable discussions centers around Dream Water's acquisition. David explains how years of cultivating relationships with strategic buyers positioned him for an eventual exit. He also shares unconventional negotiation tactics that helped keep the acquisition moving while protecting the company's financial position. The episode concludes with practical advice for founders preparing their own exits. David argues that business owners should avoid becoming fixated on valuation targets and instead focus relentlessly on building stronger companies. Enterprise value, he believes, is ultimately the result of consistently making excellent operational decisions over time. Key Takeaways Focus on execution rather than obsessing over predetermined exit valuations. Great founders create value by consistently improving business inputs. Building an entirely new market category requires patience and persistence. Data-driven retail testing creates stronger scaling opportunities. Relationships with future buyers should begin years before an exit. Legal and operational setbacks are normal parts of entrepreneurial growth. Resourcefulness often outperforms experience when building startups. Successful negotiations require understanding both your priorities and the buyer's constraints. Episode Chapters: 00:00 Introduction & Exit Readiness Resources 00:45 Meet David Lekach: Founder of Dream Water 01:20 Growing Up in a Family of Entrepreneurs 04:20 First Entrepreneurial Ventures During the Dot-Com Boom 06:00 Running a Startup from a College Fraternity House 09:00 Early Business Lessons & Viral Startup Experiences 12:00 From JD/MBA to Discovering Dream Water 14:00 The 'Anti-Red Bull' Idea: Creating a New Consumer Category 16:30 Launching Dream Water in New York City 19:00 Why David Focused on Inputs Instead of Exit Goals 20:00 Competing in a Brand-New Market 23:00 How Family Helped Scale Dream Water 25:00 Scaling Through Walgreens, CVS & Walmart 27:00 Surviving Lawsuits and Major Business Challenges 28:30 When Selling the Company Became a Real Option 30:30 Negotiating the Dream Water Acquisition 35:00 The Deal Almost Fell Apart 41:30 Lessons Every Founder Should Learn About Exits 45:00 David's Advice for Entrepreneurs Links & Resources: David Lekach Website: www.drinkdreamwater.com LinkedIn: https://www.linkedin.com/in/davidlekach/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com

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