The Exit Podcast

In this episode of The Exit, Derek Collison—creator of Cloud Foundry and founder of Synadia—shares his journey from coding at 12 to building billion-dollar cloud platforms. He discusses founding Apcera, its acquisition by Ericsson, lessons from scaling fast, navigating VC funding, and launching Synadia to power AI at the edge. His advice? Be humble, act fast, and embrace serendipity.

In this episode of The Exit: Chris Vanderzyden, CEO of Legacy Partners, helps business owners plan successful exits. After selling two of her own companies, she now guides others to avoid costly mistakes. Her firm creates “master exit plans” focusing on valuation, tax strategy, and expert teams. Chris urges owners to plan early, not wait for surprise offers. Key advice: know your EBITDA, track timing, show growth potential, and focus on net proceeds, not just revenue.

In this episode of The Exit, Sarah Hawley shares her entrepreneurial journey, from leading her family’s financial planning business to achieving multiple million-dollar exits, while navigating burnout and building a community for women entrepreneurs.

In this episode of The Exit: Edward Valaitis, founder and managing director of Edison Avenue, shares tactical insights from his extensive experience helping businesses worth $1-25 million navigate successful exits.

Paul Pappageorge, founder and CEO of Ashland Capital Advisors, shares valuable insights from over two decades of helping business owners plan and execute successful exits.

After selling his own company in 2004 and making numerous mistakes, Paul developed a passion for guiding entrepreneurs through this complex process.

Paul explains the meticulous exit planning process his firm uses, starting with understanding value drivers and realistic valuations based on industry comparables.

Mike Oleksak, Executive Director at Exit Planning Exchange, shares insights from his extensive experience helping business owners prepare for successful exits.

After starting his career in finance and management consulting, Mike co-founded the first chapter of Exit Planning Exchange in 2007, creating a network that now spans 22 chapters nationwide.

Dawn Andrews, CEO of Free Range Thinking, shares valuable insights on building systems that increase business value at exit. Drawing from her background in an entrepreneurial family, Dawn discusses how proper processes and documentation are critical for attracting buyers and commanding higher valuations.

Dawn also addresses specific challenges female founders face during exits, highlighting the need to overcome both external underestimation and internal self-doubt through meticulous preparation and confident storytelling.

She advises founders to decide on their exit timeline years in advance to shape current operations and stresses the importance of maintaining clear communication with all stakeholders during the process.

Ben Zogby, head of Flippa University, shares his journey from chemical engineer to successful entrepreneur, highlighting how he launched HighStrike, a trading education community that he sold on Flippa for $1.8M, after starting eight failed ventures. 

Ben discusses how he grew HighStrike through Instagram marketing, evolving from manual engagement to working with influencer networks, before selling through Flippa in 2022. 

After being told by a competitor in 2020 that his business wasn’t sellable, Ben spent two years systematizing operations, ultimately attracting three competing offers that increased the sale price by $300,000.

Tracy Holland, founder of Inner Fifth and Goodwill Brands, shares insights from building and selling Hatch Beauty, a company that co-created beauty brands with retailers. 

Starting with scented nail polish in her 20s, Tracy developed deep retail relationships that led to founding Hatch Beauty in 2009. 

She discusses the challenging journey of taking the company to market twice – first pulling it off at $50 million revenue when realizing rapid growth would soon hit $80 million, then successfully selling at nearly $100 million with 18% EBITDA margins.

Laurits Just, manager of Flippa Invest, shares his journey from working at BlackRock to co-founding Bits for Digits, a marketplace for partial business acquisitions that was later acquired by Flippa.

Inspired by a blog post about Basecamp’s partial sale to Jeff Bezos, Laurits and his co-founder created a platform to facilitate similar transactions for founders without direct access to high-profile investors. 

Now managing Flippa Invest, Laurits discusses their new data-driven alternative financing platform that connects accredited investors with digital business owners seeking growth capital. 

The platform allows US-registered businesses to raise between $50,000 and $1 million, with potential for oversubscription, while leveraging integrated data from sources like Stripe and QuickBooks to showcase business performance.

Jim Stevenson, founder and CEO of Bletchley Group, shares strategic insights from 25 years of advising companies through exits and acquisitions.

Jim discusses crucial aspects of preparing a business for sale, emphasizing the importance of running solid fundamentals while leaving room for buyers to see growth potential. He also highlights common mistakes that kill deals, including overvaluation, waiting too long to sell, and founder dependence.

Aaron Spivak, founder of The Founders Club, shares his entrepreneurial journey from launching a juice shop in his mother’s basement at 18 to building Hush, a premium weighted blanket company that achieved nine-figure success.

Aaron discusses how Hush innovated in response to market challenges, developing the world’s first cooling weighted blanket when faced with 70,000 competitors.

Zoe Kalar, founder and CEO of WeAre8, shares insights from her remarkable journey through three successful exits over 35 years, including one for $100 million.

Starting her first company at age 21, Zoe discusses the challenges of early exits, including painful earn-outs and misaligned values with acquirers.

She shares crucial lessons from her experiences across different markets – from her first bootstrapped company in Australia to building a transformative business in China, and later creating a data infrastructure company that became the backbone of media trading in the US.

Lindsay Pinchuk, founder and CEO of Lindsay Pinchuk Marketing, shares her journey from building Bump Club, a community-focused business for expectant parents, to its eventual exit.

Starting in 2010 as a series of local events in Chicago, Lindsay grew the company into a national brand working with major retailers like Target and Nordstrom, reaching millions of parents monthly.

Mette Dyhrberg, founder and CEO of Mymee, shares her entrepreneurial journey from her first venture in Denmark to building a successful health tech company.

Xandra Laskowski, founder and CEO of Osea Angel Investors, shares her journey from tech industry veteran to angel investor. 

After retiring in 1998, she started a family office in 2008 and began angel investing in 2013. 

Xandra discusses key criteria for startup investments, including the importance of founders having prior exit experience and maintaining two years of runway.

Kristen Cooper, CEO and founder of The Startup Ladies, shares insights on empowering women entrepreneurs to secure funding and scale their businesses. 

Starting from informal meetings, Kristen built an organization that now has 150 members across five states.

Adam Kirsch, Director at West Monroe, shares insights from his journey as both an entrepreneur and M&A advisor.

Adam emphasizes the importance of being “exit ready” from day one, highlighting key preparation steps like maintaining an organized data room, developing clear roadmaps, and building relationships within your ecosystem.

Rose Hamilton, CEO and founder of Compass Rose Ventures, shares insights from her extensive experience helping CPG brands scale and prepare for exits.

With a background at companies like Best Buy, The Vitamin Shop, and Pet360, Rose now specializes in working with founders and investors in the health, wellness, pet, beauty, and food industries.

Rose emphasizes the importance of staying connected to customers while scaling, noting that founders often lose touch with their core market as they grow.

Justin Goodbread, CEO of Financially Simple, reflects on his journey through seven successful business exits, with his most recent venture scaling to an eight-figure exit in just 49 months.

Justin discusses the alarming statistics around business exits, noting that of 11 million businesses expected to attempt selling in the next few years, only one million will successfully transact, and just 4% of those will be pleased with the outcome and exit amount.

He emphasizes the importance of understanding business value and identifying value gaps across eight key areas: planning, leadership, sales, marketing, people, operations, finance, and legal.

Scott Bushkie, Managing Partner and founder of Cornerstone Business Services, shares insights from his 26-year career helping business owners navigate successful exits.

Scott discusses the upcoming massive wealth transfer as Baby Boomers retire, with 50% expected to transfer their businesses by 2030.

He emphasizes the importance of early exit planning, comparing entrepreneurship to a marathon where initial excitement fades into a plateau.