
The Exit - Presented By Flippa
The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on https://flippa.com/the-exit-podcast/
Latest episodes

Jan 31, 2022 • 24min
Helping Entrepreneurs with Chris Heivly
Today we are talking with Chris Heivly, current Managing Director of Build The Fort, and former Co-Founder of MapQuest. Co-founding the first commercial web mapping service was Chris’s first real foray into entrepreneurship. As the Managing Director of Build The Fort, Chris helps other entrepreneurs through his books, speaking, workshops, and consulting. Fast-forward 20+ years, Chris has a lot of knowledge to share with others in the startup space.
Technology Is The Wave Of The Future
Chris has both a bachelors and a masters in geography, and he can still picture his dad’s face when he told him what he wanted to major in. His dad's response, even in the 80s, was that Chris should get into computers. Luckily, Chris did learn some computer skills and coding while studying cartography. Combining the two, he found himself writing mapping software.
Something Better Is Out There
While working for the US Department of State as the Director of Mapping, Chris says they were printing maps for National Geographic, phone books, and the like. As technology progressed, Chris developed the first CD-ROM that helped to plan trips. When the internet was the next big step in technology, the entrepreneur in Chris said there has to be a better way. That’s when he branched off on his own, threw together the URL and created MapQuest. Chris says they had no fear when creating the company, mostly because they were clueless. With their headquarters in Pennsylvania, they found they had a hard time recruiting the best talent from places like Silicon Valley. Despite their original struggles, the company did grow.
Passing The Torch
For his last three years with the company, Chris served on the board of directors. He’s a firm believer in knowing when you’ve hit your ceiling, and it’s time to move aside for someone else to take up the reins. While he helped with the lead up to going public, Chris left the company shortly before it actually happened. He says that most entrepreneurs can’t take a company from its founding to a million dollars, and that’s okay. Always stick to what you’re good at, and don’t be too proud to bring in someone to do what you can’t.
The Decision To Sell
The KPIs they were tracking were first, page views, and second, revenue. The website's traffic was what mattered most, as there were 3-4 advertising spots on each page, so page views equaled revenue. The company went public in 1999, and they found themselves asking what is the risk vs reward of going bigger. When they really thought about what the right decision for the company would be, selling was at the top of the list. Having been on AOL’s radar for several years, they thought that could be a great fit.
Where To Learn More
If you’d like to connect with Chris, he can be found on LinkedIn @ChrisHeivly. For more information on startup success, visit www.buildthefort.com.
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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Jan 24, 2022 • 28min
How Disrupting the Data Storage Industry Paved the Way for Chris Gladwin's Entry Into Data Analytics
On today’s episode of the Exit Podcast, we are talking with Chris Gladwin, the Co-Founder and CEO of Ocient. Prior to that, he had multiple successful exits, including the sale of Cleversafe, a data storage and distribution company. With plenty of venture backed partners, Chris helped to raise over $100million to grow the company. His hard work would pay off when the company sold for over $1billion to IBM. His other two exits were for Cruise Technologies, a dominant developer of Wireless Thin Clients, and MusicNow, the world’s first music subscription service. Always on the cutting edge, Chris shares with us how he started, grew, and sold each company.
Team Building
Still thinking about how to make data storage better, Chris founded Cleversafe. He built upon the techniques used in wireless communications to create a new and improved method to store and distribute the world’s data. When it came to growing the team for this core information technology company, Chris says the challenge was that it was very resource intensive. In order to hire the right people that were capable of growing this technology, Chris had to raise a lot of money. He ended up raising $100million and focused on finding his team. At the time, Motorola was collapsing and a lot of people with the right experience were looking for new jobs. Chris grabbed a lot of those people and brought them on board at Cleversafe. In addition, he brought on people he knew from his prior experiences in the space and also tapped into college recruiting. By the time IBM acquired Cleversafe they had 250 employees.
100% Conversion Rate
The main KPI Cleversafe focused on was how many qualified opportunities they were winning. Chris says they eventually got into the zone and for every potential client they got into the pilot, they were converting 100% of them. With these being multi-million dollar orders, Chris knew they had made it. The company was doing very well and Chris had no intention to sell when IBM approached him. Continuing to pursue them, IBM ultimately made an offer that Chris couldn’t refuse. With their initial approach in March 2019, by November of that year the sale would be final. Chris says the company’s investors and employees didn’t even know of the acquisition until the day before. Everyone involved was very pleased though, as the $1billion sales price meant a large financial upside for everyone. Chris recognizes that there is a lot of opportunity to not treat employees right in the sale of a company, but he’s very proud of what they were able to do for everyone.
Knowing What You Know Now, What Would You Tell Yourself Ten Years Ago?
Chris’s newest company, Ocient, is very similar to Cleversafe, so there are plenty of cheats he could tell himself, but he says he wouldn’t. Chris believes it’s the challenge that drives the satisfaction. He also does everything in a way that, even if it fails, he would have still done it because he doesn’t do it for the money, he does it because it’s his craft. So, he would tell himself only that he needs to figure it out for himself.
For More Information
To learn more about Chris’s newest endeavor, visit www.ocient.com. As they work to create the largest data analysis systems, they’re always looking for talented individuals to join the team. If you think you’d be a good fit, consider applying on their website.
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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Jan 17, 2022 • 30min
Value in Technology with Chris Boudreau
Today on The Exit, presented by Flippa, we are talking with Chris Boudreau, CEO of a start-up tech Ripe Metrics, a cannabis customer experience management platform. Chris has completed exits in several areas of the cannabis industry, including delivery, logistics, and distribution. He’s a seasoned operator that will talk to us about everything from cannabis as an emerging market to the difficulties of operating in the cannabis space.
Spotting An Emerging Market
Coming out of school with a business degree, Chris got into the banking world. He says that’s where he learned a lot about business, and he ended up at a high level. That’s when the bank collapsed during the 2008 financial crisis. Chris was only 34 and thought this might be the perfect time to start his own business. Despite not knowing the first thing about cannabis, Chris had a feeling the cannabis industry was going to really open up. He says if you get in early on an emerging market, there’s plenty of opportunity. So, he took a chance and jumped in.
Knowing What You Know Now, What Would You Tell Yourself 10 Years Ago?
Chris says the biggest mistake he’s made in the industry has to do with partnerships. He says you have to be very careful because as soon as you bring someone on it’s hard to get rid of them if they don’t work out, both emotionally and legally. So, Chris would tell himself to be way more diligent and careful with whom he chooses to partner with. He warns that it's especially hard when you’re first starting a company, and you’re eager to get people on board. Chris says he would tell himself that is the time to be especially patient.
You can find more information about Chris Boudreau at:
IG / Twitter: @subtleboudreau
Facebook: www.facebook.com/chris.a.boudreau
LinkedIn: https://www.linkedin.com/in/chrisaboudreau/
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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Jan 10, 2022 • 29min
Adding Value with Ken Harlan
In this episode of The Exit, Ken Harlan reflects the different paths that led him to where he is now. As the CEO of MobileFuse, a company focused on mobile advertising, he has started and exited multiple companies over the years. He is an advocate for learning and finding new opportunities, and he’s here to inspire other entrepreneurs to do the same.
There’s Something To Learn Everywhere You Go
Ken went to college, where he earned an accounting degree. After passing the CPA exam, Ken went into auditing, where he worked until the release of the internet caught his attention. Ready for something new, Ken went to work for a mini venture capital company where, in addition to accounting, he was permitted to sit in on investor presentations. While listening to entrepreneurs, Ken noticed it was all about relationships and references. Ken’s interests started to transition, and he decided he wanted to work for a larger technology company. At his next job, Ken learned a lot about technology before deciding he wanted to work at a dot com. He found that opportunity in running opt in lists. He wasn’t a fan of the culture there or how he was treated. One day Ken noticed a 16-year-old boy come in and the founders all fawn over him. Ken found out he was an affiliate, he owned a free stuff and coupons site. This got Ken thinking, and he searched the Internet for similar sites. The sixth site that popped up was a free and fun site with mostly broken links. Ken would buy it for $3k.
Adding Value To The Space
With his brother on board, Ken bought a few more sites. He says he would get calls from advertisers that wanted to put their coupon on his website, and he realized he could be monetizing for more. Ken had the idea of an affiliate network, which he started and then sold 18 months later. Ken says he started it because he thought it brought value and didn’t ever intend it as something to sell. As the affiliate network company grew, Ken saw that their competitor, Value Click, had just sold for a nice multiple. Having no experience of selling a company, Ken reached out to the bank that handled the transaction. They said they could easily get Ken the same results. He says they put everything together and arranged for them to meet a lot of interested buyers.
Current Projects
Ken is working on MobileFuse. To give some perspective, Ken sold his first business after 18 months and his second after 3 years, but MobileFuse he’s been with for over 10 years. He says that when he started, only half a percent of the internet was on mobile devices. They’re here to help brands and agencies to connect with others over the web in a meaningful way. They currently have over 200 clients and operate out of the US, with plans to expand to Europe and Canada.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Jan 3, 2022 • 29min
Get it in Writing with Lea Ellermeier
Today we are talking with Lea Ellermeier, an entrepreneur who has started multiple businesses and has had an impressive exit with 3M. She also is the author of Finding The Exit: It’s Not Where You Start, It’s Where You Finish. Her next endeavor is to host a podcast called Don’t Freak Out Today. She’s passionate about helping other entrepreneurs, as she has 20+ years of experience.
Useful Creations
Lea says her dad was an entrepreneur in real estate, and so she grew up seeing him run his own business and manage his own hours. Being from a small town in Nebraska, Lea always wanted to experience international business. So, her first jobs out of graduate school were in technology. She loved the world of being able to create something new, to build it, and to see it be useful. In 1999 Lea was working for a tech company that got acquired, and that’s when she made the switch to the medical device industry. There she met a guy that would go on to become her co-founder at her first company. Together they went on to start Lingual Care, which specialized in custom braces on the back of teeth. It was the first company that Lea took from creation all the way to exit.
Current Projects
Lea is still in medical technology and is working on a podcast called Don’t Freak Out Today, which is about the early stages of managing your chaos as an entrepreneur. She’s passionate about helping other entrepreneurs with the 20 years of knowledge she has gained.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Dec 27, 2021 • 24min
Angel Investing with Sanjit Singh
Today’s guest is the CEO of Adapt.io. Sanjit Singh is here to share how every exit is not the same, as he had a really cool and unique exit. He proves there are multiple ways to have a liquidity event. As a mentor to many, Sanjit has plenty of knowledge to share.
Sanjit entered the workforce in sales before he moved up the ranks at a very entrepreneurial Fortune500 company. Next he would go into medical device sales for Johnson & Johnson, where he found he didn’t like the large company environment. While working there, Sanjit spent his evening earning his MBA. Once he finished that degree, he left Johnson & Johnson in search of something smaller. He ended up starting his own company when he bought into a franchise business. He ended up receiving a large amount of money through that company due to a lawsuit in the industry. Sanjit took that money and bought another company. After building that company up, he sold it as well. Next, he decided to make an angel investment in a company that was to connect online dating to Facebook. That idea never panned out, but Sanjit became good friends with someone on the board of directors. Together they founded a tech startup called Lead Crunch, an AI driven marketing technology company.
If you’d like to learn more about Sanjit’s newest venture, adapt.io, you can visit www.adapt.io. To learn more about Sanjit, or if you’re interested in mentoring, he can be reached via his LinkedIn account.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Dec 20, 2021 • 27min
$10+ Billion Exits with Dan Caruso
Today’s guest, Dan Caruso, has had multiple $10+billion exits! Dan is the managing director of Caruso Ventures, where he specializes in investment management. From taking companies public to private, it’s all a complex process, but Dan does it all. By noticing trends early on, Dan has made some wise investments in startup companies, knows how to build one scratch, and come in and improve an existing company. He knows the value of a good team when he sees one and holds it in high regard.
Dan is a very active investor and has invested in a number of tech companies, especially those with ties to Colorado. He’s passionate about helping the next generation of entrepreneurs that are scaling businesses to get to the next level. Dan says he’s a huge believer that companies that make the biggest difference are those that are successful, tech forward, and led by inspiring people. He aims to support those companies and help them to be as successful as possible. If you’d like to learn more about Dan or what he’s up to, visit www.carusoventures.com.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Dec 13, 2021 • 33min
Selling Snow Cones in a Blizzard with Paul Wasserman
What happens when you’re ready to launch a business but receive an exit offer too good to refuse? Our next guest, Paul Wasserman, did just that. After trying various career paths, Paul decided to start his own company. He tossed around ideas with his friend for months, ultimately landing on Ebates.com, a business vision that finally came to him while on a long, mind-numbing drive. Although it had a slow start, Paul and his investors believed in it. As things began to gain momentum, the business founder was surprised to learn that 70% of users were still active after 15 years. With their future looking bright, the company decided to go public in 2013. However, that never happened because Rakuten would make them an offer they couldn’t refuse. Exiting Ebates.com in 2014 to a sum of $1 billion was an irresistible dream come true. This is his story.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Dec 6, 2021 • 30min
Investing In Yourself With Cheryl Contee Of Do Big Things
Today we’re talking to Cheryl Contee, the CEO at The Impact Seat, and the co-founder of Do Big Things. While attending Yale, Cheryl was a struggling minority scholarship student that was required to do work study while enrolled. She says the highest paying job option was in the kitchen at $17/hour, with the next highest paying job being at the help desk for $8/hour. Cheryl not only couldn’t see herself doing dishes day in and day out, but she knew taking that pay cut would allow her to learn a lot more. She says she learned so much about technology and customer service that she knew it was the right decision. If the willingness to learn is there, you should always invest in yourself.
Cheryl is working on the second edition of her book, Mechanical Bull: How You Can Achieve Your Startup Success. She calls it the book she wishes she had when she was starting out. The book goes through the full life cycle of a startup and the new edition will have a preface that talks about current times. The audiobook version will be out later this year and available on Amazon.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Nov 29, 2021 • 31min
Keeping An Open Mind With Serial Entrepreneur Deanna Brown
Today we’re talking to Deanna Brown, a serial entrepreneur who has had multiple successful exits. Starting in the media business, Deanna quickly found a love for being an entrepreneur when she helped to launch the website, Epicurious. She’s been through a variety of different exits, but says a solid team has always been a strong selling point. Through an open mind approach, Deanna has been able to see great success in starting, growing, and selling businesses.
Deanna says she has lots of interesting and exciting projects coming up. She says she believes in change and thinks that change is the most important thing the world needs right now. She looks forward to being a part of that change and encourages listeners to tune in to her LinkedIn profile at www.linkedin.com/in/deannacbrownsf/ where she will be making some big announcements soon.
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The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/