Eckfeldt + Associates

From Angel to Exit

Episode Archive.

Every conversation since the show began in June 2025, newest first. Founders, investors, and advisors talk through what really happens when you build, scale, and sell a company, including the parts most people only learn the hard way. Each episode page has the full video and a summary, and most have a full transcript. Filter by topic, or search for a guest, a company, or a subject.

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From Angel to Exit, episode 58, with Kyle Ewing

From Founder Dependence to Freedom: How to Build a Business That Thrives Without You Episode 58, with Kyle EwingListen now →

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Episode 58Sep 23, 202644 minScaling and Growth
From Founder Dependence to Freedom: How to Build a Business That Thrives Without You
Kyle EwingChairman, Windward Equity

Why lasting value comes from learning from failure, protecting cash, building systems and the right team, and knowing what you want the business to give you.
Episode 57Sep 2, 202643 minDeals and M&A
Worried About Your Exit? How to Use an ESOP to Create Liquidity, Tax Benefits, and Employee Wealth
Lawrence KaplanManaging Director, CSG Partners

How an ESOP lets owners take money off the table without selling the whole company to private equity or a strategic buyer.
Episode 56Aug 26, 202641 minExit Readiness
Exit Planning Starts Early: Strengthen Financials and Leadership to Maximize Business Valuation
Dan BauerFounder, The MBA Exchange

What makes a business valuable to a buyer, and the everyday decisions that quietly make an exit harder.
Episode 55Aug 19, 202642 minExit Readiness
Can Your Revenue Scale? Five Questions That Strengthen Your Business Exit Strategy
Rick McPartlinRevenue science expert

Why buyers care where your revenue comes from, whether it repeats, and how the business can grow it after the deal.
Episode 54Aug 5, 202647 minScaling and Growth
How Dream Water Created a New Consumer Category and Achieved a Successful Exit
David LekachFounder, Dream Water

How solving problems better than anyone else built a new consumer category and carried it to a successful exit.
Episode 53Jul 29, 202642 minExit Readiness
Why Custom Systems Hurt Your Exit, and What Founder-CEOs Should Build Instead
Yarin GaonSerial entrepreneur

Why more products, customers, and revenue streams can lower value, and what to build instead.
Episode 52Jul 15, 202638 minExit Readiness
How Systems, AI, and Customer Experience Drive Higher Business Valuations
Christine McDannellFounder, The Magnolia Firm

Why buyers pay more for a business that runs without its founder, and how systems and AI get you there.
Episode 51Jun 24, 202644 minDeals and M&A
How Founder-Led Companies Navigate Acquisitions Without Losing Top Talent
Jennifer FondrevayFounder, Day 1 Ready

Why people, not financial models, decide whether an acquisition delivers the value everyone expected.
Episode 50Jun 3, 202647 minLife After the Exit
The Exit Readiness Mistake Most Founders Make Before Selling Their Business
Ana ChaudFounder, Garden Bar

The story behind Garden Bar, and what she learned scaling, selling, and moving beyond founder life.
Episode 49May 14, 202641 minScaling and Growth
The Leadership Hiring Strategy That Helped Scale and Successfully Exit Twice
Carl KutsmodeExecutive recruiting entrepreneur

How the right leadership hires helped him scale and exit two businesses in talent acquisition.
Episode 48Apr 29, 202652 minLife After the Exit
What Jeff Corn Learned About Co-Founders, Exit Strategy, and Who You Are After the Deal
Jeff CornFounder, Virtuance

A candid look at building Virtuance, selling it, and the questions of identity that follow the deal.
Episode 47Apr 22, 202642 minExit Readiness
Unprepared for a Business Exit? Use Strategic Planning to Maximize Valuation Outcomes
Laurie BarkmanFounder and CEO, Business Transition Sherpa

What to do when an unexpected acquisition offer arrives before you are ready for it.
Episode 46Apr 6, 202645 minBuyers and Investors
Struggling to Maximize Exit Value? Master Buy-Side M&A Strategy for Higher Valuations
Clay RisherManaging Director, TrueNorth Capital Partners

How buyers actually think, and how founders can use that to run a better sale process.
Episode 45Mar 4, 202644 minDeals and M&A
Can't Find a Clear Buyer for Your Niche Business? Reframe the Story to Create an Exit Path
Johnny LeHaneExited founder and investor

How WAKA grew from a bar-napkin idea, and how to find an exit when a business is not built to sell.
Episode 44Feb 25, 202639 minExit Readiness
Struggling to Attract the Right Buyer? Position Your Company Early to Maximize Exit Value
Elizabeth SheaFounder, SpeakerBox

How positioning a company early shapes which buyers show up and what they will pay.
Episode 43Feb 18, 202648 minBuyers and Investors
Inside Private Equity Due Diligence: What Founders Must Fix Before an Exit
Chris MarescaSeven-time exit founder

What private equity buyers dig into, and what founders must fix before they go to market.
Episode 42Feb 10, 202649 minLife After the Exit
The Hidden Psychology of Selling Your Business: Prepare for Exit Without Regret
Denise LoganAuthor, The Seller's Journey

Why the emotional transition is the riskiest part of a sale, and how to prepare for it.
Episode 41Feb 3, 202641 minBuyers and Investors
Too Small to Sell? The Strategy Renovus Uses to Turn Micro-Caps into Market Leaders
Lee MinkoffManaging Director, Renovus Capital Partners

How private equity looks at founder-led service businesses that seem too small to sell.
Episode 40Jan 26, 202645 minScaling and Growth
The Invisible Rules of Credibility: Inside Ujwal Arkalgud's Journey to a High-Margin Exit
Ujwal Arkalgud

How cultural insight won Fortune 500 clients and turned a services firm into a high-margin exit.
Episode 39Jan 20, 202648 minDeals and M&A
From Lifestyle to Legacy: How Strategic Acquisitions Multiplied This Agency's Value Before Exit
Peter Lang

How buying other companies helped him scale faster and exit several businesses without outside capital.
Episode 38Jan 12, 202644 minScaling and Growth
From Bankrupt to $8M EBITDA: How Tim Murphy Revived Boomer Parks with PE Discipline
Tim MurphyFormer CEO, Boomer Parks

How a bankrupt amusement park group became a profitable business ready for private equity.
Episode 37Jan 7, 202643 minLife After the Exit
Why 75% of Founders Regret Selling, and How to Avoid It with Better Planning
Scott SniderPresident, Exit Planning Institute

Why he faced an identity crisis after selling at 24, and how founders can avoid regret after the sale.
Episode 36Dec 29, 202544 minDeals and M&A
Outgrown the Broker, Ignored by the Banker? How to Sell in the Lower Middle Market
Karl SigeristManaging Director, Shaughnessy Group

Why so many lower middle market deals fail, and how to prepare for a high-value exit.
Episode 35Dec 22, 202543 minExit Readiness
Avoiding the Shiny Penny: How to Stay Focused and Maximize Your Business Exit
Walter Paulsen

Lessons from turning down an offer and decades of founding, scaling, and selling in Silicon Valley.
Episode 34Dec 15, 202543 minDeals and M&A
Earnouts, Exit Fatigue, and Valuation Games: A Founder's Guide to Surviving M&A
Mital MakadiaPartner, Grellas Shah

The legal and strategic mistakes founders most often regret at exit, and how to avoid them.
Episode 33Dec 8, 202547 minDeals and M&A
Inside a Founder's Exit Journey: Structuring for Scale, Earning Trust, and Choosing the Right Buyer
Wesley PortegiesFounder, MedComms Experts

How building solid systems prepared his firm for an exit before he ever planned one.
Episode 32Dec 1, 202542 minScaling and Growth
How Founder Complacency Kills Value, and What Scott Allison Did Differently
Scott AllisonCo-founder, Allison Marketing

How he scaled a boutique PR firm into a global agency, and why complacency costs founders value.
Episode 31Nov 24, 202544 minDeals and M&A
How to Avoid Deal Disasters: Why Founder-CEOs Need a Dedicated M&A Lawyer Before Selling
Chad WilliamsPartner, Lamb McErlane

Why every founder needs an M&A lawyer, and how to handle LOIs, earnouts, and non-competes.
Episode 30Nov 10, 202544 minScaling and Growth
From Broke to Multi-Exit Founder: How Solving Real Problems Built Two 7-Figure Companies
Travis LutherFounder, Moso Pillow

How building and selling Queen Anne Pillow and TrialLine both started with solving a real problem.
Episode 29Nov 3, 202546 minLife After the Exit
Founder Fatigue, Deal Drama, and the Power of Values in a Successful Business Exit
Gregg LedermanFounder, A Great Life Now

The emotional toll, deal setbacks, and values behind selling his SaaS company to a global buyer.
Episode 28Oct 23, 202543 minScaling and Growth
Burned by Broad Services? How Specialization Scaled Pedestal Search to a Successful Exit
Aaron LevenstadtFounder, Pedestal Search

How narrowing services and understanding buyers led to a successful agency exit.
Episode 27Oct 13, 202550 minScaling and Growth
Struggling With Niching? How Erik Olson Used SEO and Structure to Scale 3 Agencies
Erik J. OlsonFounder, Array Digital

How niche verticals, systems, and recurring revenue helped him build three agencies.
Episode 26Oct 6, 202547 minDeals and M&A
How to Sell the Same Company Twice, and Exit With More Every Time
Matthew PorterCo-founder, EONOVA

How he bootstrapped a data center company, grew it through acquisition, and sold it twice.
Episode 25Sep 29, 202546 minDeals and M&A
How to Buy 24 Companies with No Cash and Sell for a 14x Multiple: John Ratliff's Playbook
John RatliffFounder, Appletree Answers

How a call center business grew through 24 acquisitions and sold at a 14x multiple.
Episode 24Sep 22, 202542 minExit Readiness
Think You're Exit Ready? Neil Schaffer's 1,000-Day Rule Will Change Your Mind
Neil SchafferCEO, Carlton Advisors

What it really takes to exit well, and why preparation starts a thousand days out.
Episode 23Sep 15, 202544 minScaling and Growth
How Robert Heil Doubled Growth by Rebuilding Strategy Around Client Value Creation
Robert HeilCEO, Financial Aid Services

Lessons from scaling EdTech ventures, leading M&A deals, and taking the CEO seat after a founder exit.
Episode 22Sep 8, 202548 minLife After the Exit
How Bootstrapping With $1,500 and Cold Calls Built a Multi-Million Dollar Ad Business
Matthew Diteljan

How a $1,500 startup became a national ad platform, and the hard lessons from a buyout and burnout.
Episode 21Sep 1, 202542 minDeals and M&A
Facing a Runway Crisis? How Employee Deferrals Secured Roy Vella a Successful Acquisition
Roy VellaCo-founder, NetAbacus

How his team kept the company alive after a lost funding round and still reached an acquisition.
Episode 20Aug 25, 202538 minLife After the Exit
Struggling to Scale Your Expertise? How Thomas Michael Turned SAP Training into a 7-Figure SaaS Exit
Thomas Michael

How he scaled an online training company, sold it with no earnout, and what came after.
Episode 19Aug 18, 202539 minExit Readiness
Managing Mid-Performer Assets: A Tactic for Founders Facing M&A Stagnation
Frank WilliamsonCEO, Oaklyn Consulting

What to do when a business performs decently but falls short of its growth or exit goals.
Episode 18Aug 11, 202551 minDeals and M&A
From Near Bankruptcy to 10X Exit: How Sam Arman Mastered the Art of Selling Businesses
Sam ArmanSerial entrepreneur

How he built and sold several companies, some under pressure and one for a 10x private equity exit.
Episode 17Jul 28, 202537 minScaling and Growth
Building Brand Equity for Scalable Growth and Maximizing Business Exit Value
Lysle WickershamAgency founder

How brand equity drives enterprise value, from scaling a $170M agency through several exits.
Episode 16Jul 28, 202539 minBuyers and Investors
Inside 47 Acquisitions: What Experienced Buyers Look for in a Successful Acquisition
David TurnerCEO, Velocity Now

What a buyer behind 47 acquisitions looks for, and what really drives a successful exit.
Episode 15Jul 21, 202545 minScaling and Growth
How Leslie Adams Scaled and Sold a Multi-Generational Scrap Metal Business
Leslie Kraatz AdamsFounder, A Work of Heart

How she grew a third-generation family business and carried it through an exit.
Episode 14Jul 14, 202540 minDeals and M&A
Inside a Rapid M&A Deal: How Calvin Johnson Prepared Lykki for a Fortune 500 Exit
Calvin JohnsonFounder, Lykki

How he built an office supply and coffee delivery company and sold it to a Fortune 500 buyer.
Episode 13Jul 7, 202537 minBuyers and Investors
Inside Cannabis Private Equity: Scalable Models, Smart Terms, and Investor Strategy
Jordan YoukilisFounding Partner, Key Investment Partners

The challenges and opportunities founders face when they raise from cannabis investors.
Episode 12Jun 30, 202545 minLife After the Exit
Lessons from Four Exits: How Pete Martin Built, Scaled, and Sold Without Regrets
Pete Martin

Lessons from four exits, including a 12x EBITDA sale to KPMG.
Episode 11Jun 23, 202536 minScaling and Growth
How Alan McLaren Scaled Two Agencies, Built a Personal Branding Powerhouse, and Prepped for Exit
Alan McLarenCo-founder, Strata Originals

How he scaled two agencies and now helps founders build a personal brand ahead of an exit.
Episode 10Jun 16, 202552 minDeals and M&A
Behind the Exit: Lessons from Ross Shanken's Nine-Figure Journey with Jornaya
Ross ShankenFounder and former CEO, Jornaya

The frameworks and hard moments behind building Jornaya and guiding it to a nine-figure exit.
Episode 9Jun 16, 202544 minScaling and Growth
From Coffee Brand Success to Corporate Governance Mastery: Joshua Maidan on Scaling and Exiting Right
Joshua MaidanEntrepreneur and investor

How he built a premium coffee brand, and what good governance means for scaling and exiting.
Episode 8Jun 16, 202543 minDeals and M&A
Inside Middle Market M&A: What Every Business Owner Must Know Before Selling
Bill SnowManaging Director, Focus Investment Banking

Blunt truths about middle market M&A from nearly two decades on the inside.
Episode 7Jun 16, 202544 minDeals and M&A
Lessons from a Failed M&A to a Successful Exit: The Founder Story Behind ClassTag
Vlada LotkinaFounder, ClassTag

How a failed deal set up a successful exit for her EdTech company.
Episode 6Jun 16, 202545 minDeals and M&A
From Side Hustle to Strategic Exit: Lessons from Scaling Unique World
Eddie GellerFounder, Unique World

The road from early web services to a high-stakes M&A exit.
Episode 5Jun 16, 202550 minScaling and Growth
From Bootstrap to Buyout: Scaling Tech Startups with Strategic Go-to-Market and Exit Fit
Shreesha RamdasSerial entrepreneur

His startup fitness framework and lessons from building and selling several tech companies.
Episode 4Jun 16, 202545 minScaling and Growth
How Shawn Freeman Scaled an MSP to $5M and Exited at 1.4x Revenue
Shawn FreemanMSP founder

How a tech side hustle became a $5M managed services business and sold at 1.4x revenue.
Episode 3Jun 16, 202539 minExit Readiness
From Clarity to Close: Strategizing Your Ideal Business Exit
Suren KapseM&A and exit strategy advisor

How founders can get clear on the exit they want and prepare to close it.
Episode 2Jun 16, 202547 minBuyers and Investors
Unlocking the Second Bite: Maximizing Business Exits
Todd TaskeyM&A advisor and angel investor

How to structure cash, equity, and earnouts, and get a second bite with private equity.
Episode 1Jun 16, 202545 minLife After the Exit
From Founding to Exit: Scaling Mass Communications and Life After
Darren MassFounder, Mass Communications

His path from launch to acquisition, and what life looks like after the sale.