Build Better Business Podcast with Chuck Crumpton

Lee argues that private equity has been "like shooting fish in a barrel" for the past 20 years, benefiting from low interest rates and rising asset multiples. Those conditions have changed, and the result is a backlog of roughly 33,000 businesses worth approximately three trillion dollars that PE firms cannot sell profitably. He says firms must get involved from day one, understand the data, asses...

Adam turned a short trip to the Philippines into a 16-year stay, during which he built a business and learned how low-cost global destinations can expand a company's bottom line and capabilities. He cautioned that businesses rushing to implement AI must first get their processes correct, warning that poor inputs produce poor outputs. We discuss the risk of over-reliance on a single client. I share...

Janessa launched her wedding business and had her first customer within two weeks, grew rapidly to $7 million in revenue across 37 destinations, and conducted over 14,000 weddings. She talks transparently about how Covid and cancer greatly impacted her life and business. A defining feature of the business was that it was built from day one with the explicit intention of selling to The Knot Worldwi...

Jay's pivot to private money began in January 2009 when his bank, without warning, closed his line of credit during the global financial crisis, leaving him unable to fund two properties he had under contract. Within 90 days of applying what he learned, Jay attracted over $2,150,000 in private funding without ever directly asking for money, and his business tripled in 2009. Jay draws a clear disti...

Randy cautions that founders who are burned out are often the least well-positioned to sell, because desperation leads to poor outcomes and the company is typically not at peak value during a difficult stretch. Most founders Randy has spoken with waited too long to sell and too long to prepare. Beyond founder dependency, contractual weaknesses are among the most common issues uncovered during due...

The central theme of the conversation is how improv comedy thinking can transform business culture. Kathy explains that doing improv and standup gave her skills in risk-taking, adaptability, and confidence, and she eventually founded Keeping It Human to merge those two worlds. She argues that most companies talk about innovation but fail to create cultures where employees feel safe enough to take...

Eva discusses how she found her life's purpose, which centres on promoting diversity, with a specific focus on women and single parents, drawing on her own experiences as an immigrant and single mother.  She credits COVID-19 as the period of reflection that clarified this purpose for her. Her aha moment came when she noticed the dramatic underrepresentation of women in leadership within research a...

 Luca is an Italian-born research scientist who lives in Boston, with a degree in AI from the University of Edinburgh, a PhD in AI and robotics from Cambridge, and postdoctoral work at Cambridge, Harvard, and Mila, currently working at Sapient Intelligence.  Luca says he sees himself as a lifelong learner and chose AI because it can be applied across many domains, giving him “windows” into fields...

Lou Kennedy’s road to success has been anything but easy. Even recently, she faced significant external challenges that threaten the billion-dollar enterprise she worked so hard to build. But Lou is a friend, a fighter, and someone whose character, competence, and relentless determination have carried her through adversity before—and I have every confidence they will do so again. Most of us who ha...

Quentin explains he was originally inspired to pursue AI by the movie “The Matrix,” studying computing science and AI in the early 2000s when symbolic AI and expert systems dominated, then continuing into a PhD and a long career in the field. He highlights a core problem for businesses: generative AI is powerful for language tasks but not suited for some tasks.   He cites an MIT report that found...

Jeff stresses that entrepreneurship is a “vertical mountain climb with no equipment,” and that many people will not figure it out despite their best efforts, which must be acceptable. He quit a comfortable partner role at a venture fund the day he returned from his honeymoon, with no plan and earning only about $3,000 in his first year, leading to intense personal and marital strain before he even...

Ron describes a pivotal “aha” moment during his early corporate career in Atlanta. Stuck in traffic on I‑85, he looked at the empty expressions of commuters around him and felt a pit in his stomach, realizing he didn’t want that to be his life, even if his salary doubled or tripled. His core message is that success is less about intelligence or money and more about persistence: “you can only lose...

Shay Houser is one of the smartest and most vunerable people I know, and I'm honored to call him my friend. Battling and overcoming major addiction struggles, he went on to do over $1B in M&A deals. We talk life and business in this episode. I asked what advice Shay has for people “stuck” in comfortable corporate jobs who feel an entrepreneurial itch. His response is blunt: if it’s truly their...

Andrea expects AI will surpass humans in many tasks before 2040, but sees the real tipping point as when AI combines high competence with the ability to interpret real‑world context like a human (e.g., distinguishing genuine clinical depression from temporary sadness), something current systems cannot do because they must treat user input as true. On global AI governance, he says there is no “magi...

Matt outlines what separates great from average communicators: they are audience‑centric (“it’s about them, not about you”) and deliver clear, concise messages with good structure.  Discussing the book, Chuck highlights a key line: the goal is not perfection but being clear, confident, and connected.  Listen to hear Matt's six key principles from “Think Faster, Talk Smarter” Let me know how I can...

Kelly has an impressive background - she's originally from New York City with undergraduate and master's degrees from NYU, plus post-graduate work at Harvard and Columbia. She is a classically trained actor who performed mainly on stage. I'm honored to call her my friend. Kelly founded Win the Room (WTR) at a crossroads in her career, not wanting to return to acting or Wall Street. She began helpi...

Andres has an MSA and MBA from Ohio University and wrote a book called "Persuade: The Four Step Process to Influence People and Decisions" The most critical element in negotiation is thorough preparation, which not only provides information but builds confidence. Andres emphasizes that "nothing convinces like conviction" and proper preparation creates the confidence needed for effective negotiatio...

At SAF, we help folks buy and sell great companies and build in the process. Most see a 5-7x ROI because of the work we do. Let's set up a call to discuss. Enjoy my conversation with Harry! Harry T. Jones describes himself as "living a life of second and third chances" - he's in his third career and second marriage. He spent over 20 years in food manufacturing as a CEO and emphasizes that "the mos...

In addition to being one hell of a business leader, Leland is a husband, father, and my friend. I highly recommend you visit his very impressive gallery in Hillsborough, NC.  LelandLittle.com The auction business has undergone significant transformation over Little's 35-year career. Market preferences have shifted from 18th and 19th century antiques (popular in the 1980s-1990s) to mid-century mode...

Captain Mike Penn flew 87 combat missions until he was shot down and had to eject at 500 miles per hour. From being a POW at the "Hanoi Hilton" in Vietnam, to becoming the Chief Pilot at Southwest Airlines, to battling addiction, Mike shares his incredible life story. This episode moved me like few have. You will be drawn to his transparency, humility, candor, and demeanor.  Please enjoy and let m...

John Sterling is a Citadel University graduate (BA in Political Science, 1983) who led Datastream to a $200 million exit. He currently serves as CEO of Sterling Ventures Group, which "buys and grows B2B SaaS companies quietly and intentionally". His portfolio includes Sterling Sales (sales coaching and training). John's sales training approach addresses multiple components beyond just training sal...

Most of my clients have a HUGE question for me - What is my business worth? Scott, a subject matter expert in valuations, sheds some interesting light on the topic. If I can help you get some real numbers on your business, let me know. It's a big deal. Scott emphasizes that business valuation is both a science based on accepted principles and an art involving numerous assumptions. He notes that fi...

 Karl emphasizes that leaders often assume everyone thinks and is motivated the same way they are, which he describes as the "human condition". He advocates moving from the "golden rule" (treat others as you want to be treated) to the "platinum rule" (understanding what motivates each individual). When asked about the biggest organizational breakdown, he identifies trust as the primary issue. Karl...

Todd emphasizes the importance of authenticity in leadership and speaking, sharing that he strives to be genuine rather than polished, making fun of himself and discussing failures rather than just successes. Todd also vulnerably shares that his wife died five months ago, describing how he relied on his team during this difficult period. 3 big takeaways from his book "Dancing with Monsters" Fear d...

The pivotal moment came when Chris analyzed his father's retirement situation in 2005. Despite his father doing "everything right" - contributing to his 401k, paying off all debt including his house, and being completely debt-free at 61 - Chris calculated that his father would run out of money in 5-6 years if he retired. This realization led Chris to question the traditional financial advice he wa...