E15: Today I have a special guest, friend, and forward-thinking entrepreneur, Chris Meso.  In 1989 while still in his twenties, Chris founded Mobile Air, which after more than 30 years of growth has become the largest private, portable HVAC specialty services business in North America. What's special about Chris's story is that not only did he know the right time to sell the business, but Chris also helped the private equity firm who acquired his business envision a strategy to roll up his competitors.

Chris believed so much in this roll up strategy that he negotiated significant equity in the overall business platform, which created a substantial "second bite of the apple" for him when the private equity firm sold the platform just two years later.  On today's episode, Chris and I talk about the importance of preparing to sell a business and choosing the right buyer with the right strategy to maximize your ultimate outcome.

Today, Chris runs T Rex Advisory helping business owners implement simple, proven organizational frameworks to tone down chaos, earn more and go back to falling in love with their business.

A few highlights:

(4:30) ... Working in an ultra-competitive industry and building the moat that changed his future

(11:15) ... Trying to understand what Mobile Air was worth

(22:53) ...  The Kumbaya Dinner, and negotiating the next bite of the apple

(29:44) ... As an entrepreneur, "I left nothing on the field...  and got off the field at the right time to enjoy the fifth quarter of my life."

I hope you enjoy my conversation with Chris.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E14: Today we have a special guest and good friend of Exitwise, Joe Chura.

Joe has had an incredible entrepreneurial journey starting on the Ford Motor Company assembly line to founding two automotive digital marketing platforms, which he sold to cars.com in 2018 for a walk off home run outcome. Joe is an exceptional leader, marketer and lifelong learner who has taken on many different challenges well beyond the businesses he's most widely known for.

He's recently run a marathon, hosts an incredible podcast called, Not Almost There, and he recently launched a new non-alcoholic brewery Go Brewing in Illinois. 

A few highlights:

(10:35) ... Working at an auto dealership during the day, and building a digital marketing company at night

(36:34) ... September 28, 2017 - a Wedding Anniversary, and a fateful phone call from Cars.com

(45:50) ...  October 31, 2017 - Halloween, and the most important text of his professional life 

(1:07:42) ... what success means to Joe, and what surprised him most after the sale of his business.

(1:11:18) ...  the launch of Go Brewing 

I hope you enjoy my conversation with Joe Chura.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E13: This episode is Part II of a two-episode series.  If you haven't listened to Part I, we invite you to listen to it first before enjoying this episode.

Today, based on multiple requests from our listeners, my friend, fellow entrepreneur, and co-founder of Exitwise, Brian Dukes is going to interview me, Todd Sullivan, to help our listeners learn a little bit more about my background and how we came to start Exitwise. We'll take you through the four companies I've started and sold while sharing a few memorable stories about my co-founders, investors, customers, and acquirers that have made my professional journey worth the risk, the sacrifices, and the emotional rollercoaster that is entrepreneurship.

A few highlights:

(3:53) ... How Todd found himself on the "Tech Crunch 50" stage with Jason Calacanis

(9:19) ... How Peter Karmanos helped Todd get Crowd Zone installed in the Carolina Hurricanes stadium

(22:02) ... Getting Dan Gilbert's business card, and how Dan helped Todd relaunch Spirit Shop

(33:42) ... The creation of Exitwise

We hope you enjoy our conversation.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E12: Today, based on multiple requests from our listeners, my friend, fellow entrepreneur, and co-founder of Exitwise, Brian Dukes is going to interview me, Todd Sullivan, to help our listeners learn a little bit more about my background and how we came to start Exitwise. We'll take you through the four companies I've started and sold while sharing a few memorable stories about my co-founders, investors, customers, and acquirers that have made my professional journey worth the risk, the sacrifices, and the emotional rollercoaster that is entrepreneurship.

A few highlights:

(9:36) ... How professional hockey led to the creation of the first big product of Todd's career

(18:10) ... The creation of Capball, a meeting with Toys R Us, and a chaotic trip to pitch the product

(29:03) ... The Michigan (Ross) MBA program, and the creation of Spirit Shop

This is the first part of a two-part series. We hope you enjoy our conversation.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E11: Today I have a special guest friend and former personal mentor, Jeff Ma.

Jeff is best known as a former member of the MIT Blackjack team who won millions in the mid 1990’s. Jeff's success was the basis of the main character of a New York Times bestselling book, “Bringing Down The House”, and the highly successful movie “21”. Because of his focus on data and analytics, Jeff's success at the blackjack table translated well into his prolific entrepreneurial career.

Jeff and his teams built and sold Circle Lending to Virgin, Citizen Sports to Yahoo, and finally, tenXer to Twitter.  Jeff has worked as a consultant to the San Francisco 49ers, the Portland Trail Blazers and a major sports apparel brand, helping them to make better decisions using data and analytics. His most recent book, "The House Advantage: Playing the Odds to Win Big in Business"​ was a business bestseller and draws on his unique experiences at the table and in the sports world creating a truly accessible work about business analytics. Jeff is passionate about how data and better visibility into one's performance can make people better.

In this week's episode Jeff discusses how his experiences at the blackjack table helped him build valuable companies and how he knew when to pick up his chips, leave the table and cash out.  A few highlights:

(10:00) ... losing $100K in 5 minutes at the blackjack table

(15:45) ... the analogy of blackjack to startup life and building a business - hanging around long enough to sell your company is no different than a card counter having enough chips to catch a hot streak.  

(27:00) ...  why getting congratulated at the beginning of a founder journey may be the wrong message to send.  Raising venture capital shouldn’t always be the celebratory moment it often is for entrepreneurs 

(43:00) ... acquisition values, and why they're often misreported and misunderstood in the media

I hope you enjoy my conversation with Jeff Ma.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E10: Today, I have a special guest, friend - home improvement entrepreneur, Brian Elias.  With just $5K in savings, Brian started and built 1-800 Hansons, a company selling replacement windows, siding and roofing in the Midwest. Brian built Hansons to more than $70M in sales and today Hansons is one of the top 10 home improvement companies in the US. In 2017 Brian sold the majority of his share in Hansons to a private equity firm, Huron Capital.

Brian is a marketing genius who understands how to connect with people on a personal level and he is always willing to give back to his fellow entrepreneurs.  Today Brian and I chat about his decision to sell his business, how he prepared his business to maximize his sale price and his decision to roll some of his equity back into the business alongside his buyer in hopes of a second liquidity event.

I hope you enjoy my conversation with Brian Elias.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E9: Today I have a special guest, friend and prolific entrepreneur, Jay Adelson.

Jay is a serial entrepreneur, having co-founded and built countless significant companies over the last 20+ years: 

• Founded Equinix (EQIX) in 1998, eventually helping drive to a successful IPO 
• Helped launch Digg, Inc. and providing initial business strategy, taking the role of CEO beginning in 2005
• Co-founded Revision3, holding roles of CEO and then as Chairman until their sale to Discovery Communications
• CEO of SimpleGeo, and led the sale to Urban Airship in November, 2011
• Co-founded Opsmatic, serving as Chairman and led the sale to New Relic in October, 2015
• Currently serves as Chairman and Co-founder at Scorbit, a connected gaming company
• Currently a Co-founder and General Partner of venture firm Center Electric, LLC

Jay's incredible entrepreneurial talents are second to none, so it comes as no surprise that in 2008, Time Magazine named Jay one of the Top 100 Most Influential People in the World.

Jay shares some of the lessons he's learned so we can all be a little smarter when it comes time to sell our businesses someday.

I hope you enjoy my conversation with Jay Adelson.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E8: Today I have a special guest and friend who's been through an IPO and sold his last company to Microsoft.

Stephen Cox created his first success as an early employee at PurchasePro, a B2B eCommerce platform, which went public in 1999. Steven followed that up by building TakeLessons, an online music lessons platform to help other musicians and educators connect with students in person and online. Steven, his team and his investors did not find instant success with Take Lessons, but they never gave up.

And 14 years later, having raised 19 million from 14 different investors in three rounds, his company TakeLessons became one of the largest live educational sites on the web and was purchased by Microsoft in 2021. 

Steven Cox shares how he was able to earn, in his words, the emotional equity to convince his board to increase the equity share for some key employees and co-founders of TakeLessons who are not only instrumental in building the take lessons business, but who are critical in making the sale to Microsoft happen.

Today's episode is for founders who may find themselves needing to ask investors and their board for a bigger piece of the pie for key employees or themselves to get everyone aligned around the sale of a business.  I hope you enjoy my conversation with Steven Cox. 
the best decisions.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E7: Brandon started in investment banking at Goldman Sachs and then jumped to private equity to learn the tricks of the trade. After graduating from Harvard Business School, Brandon not only started a company, but he also worked in strategy and in M&A roles in multiple industries. Ultimately, Brandon discovered his life changing opportunity as an independent sponsor by purchasing and rolling up dental practices in the Midwest.

Five years later, after building up a significant business, Brandon and his partner were approached by a much larger organization to be acquired.

For many independent sponsors, buying a business takes incredible skill, patience and persistence.  Success does not happen overnight, and it takes real sacrifice.  Brandon's story is one of systematic and tireless pursuit of improving his personal business skillset while diligently searching for his big opportunity.

We hope you enjoy our conversation with Brandon Halcott.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/ 

E6: Larry is a recognized industry expert in the field of Customer Experience and the author of two books, Managing Forward and recently published Innovating Analytics.

Larry founded ForeSee Results to provide multichannel customer satisfaction analytics and analysis to clients worldwide in a variety of industries including retail, government, healthcare, finance, education and more. Larry grew the company from inception to a successful exit at the end of 2013. 

In this episode, Larry tells the story of an extremely complicated dual sales process - preparing the company for IPO while also negotiating with a Private Equity firm on a full sale of the business.  Listen to hear how Larry managed both paths, and how the story eventually turned out.

We hope you enjoy our conversation with Larry Freed.

The Wise Exit is an Exitwise Production. Are you a business owner looking to sell your business faster, for more, and with less complexity? Learn how Exitwise's founder-led team helps you maximize your exit value and simplifies the M&A process: https://exitwise.com/