The Mindset of an Entrepreneur with 3 Exits

On the Let’s Grab Coffee podcast, Sampford Advisor’s George Khalife sat down with Dennis Mortensen who’s the Founder & CEO of to chat about entrepreneurship, artificial intelligence, and exits.

To give you context, Dennis is an expert in leveraging data to solve enterprise use cases and a serial entrepreneur who’s successfully exited several companies on that theme. His long-term vision of killing the inbox led to the formation of and the creation of Amy + Andrew, artificially intelligent assistants who schedule meetings.

Previous to starting, Dennis founded four different ventures – three of which had successful exits and one of which went bust (which he argues was rather an expensive MBA). Here’s a glance at his past portfolio:

·       In 1996, Dennis founded Canvas Interactive – a full service digital agency with a strong taste for analytics. The company was acquired by TJ Group in 2000.

·       In 2002, Dennis founded evonax – think OpenTable/Seamless for Europe (with a twist). This company went bust.

·       In 2004, Dennis founded Indextools which offered enterprise web analytics. The company was acquired by Yahoo! in 2008.

·       In 2010, Dennis founded Visual Revenue which provided predictive analytics for media. The company was acquired by Outbrain in 2013.

·       Dennis founded in 2014 – since then, the company has raised $44.3M (according to Crunchbase) with 54 people on the team.

During the podcast, George asked Dennis how he was able to achieve success with three exits and continue on a similar path with his current venture, Here’s what Dennis said:

“I am certainly not sold on this idea that you start a venture with some idea of what the exit will look like. I can empathize with that slide on your deck where you describe what the end game would look like, but certainly the purist within me wants to embark on a mission for where there is really no surrendering along the way. So everything which I’ve started, I started with the idea that this can be a single, stand-alone viable business. It was never one for where I set out with the idea that here’s a nifty little feature for Gmail and if I put a team together Google might give me $10 for it, that’s never really how I thought about it.

What I do think is important though is for a founder to sit down and plan what milestones lie ahead for my venture. At some point, you might get to the realization that you are not the best fit to continue growing the venture any further and there’s nothing wrong with that.”


If you run a good business, you will certainly get opportunities along the way.


When talking about the relationship founders should have with investors or advisors, Dennis adopts the ideology that these people are supposed to be partners…and if you want to find good, trustworthy partners you should get to know them over a longer period of time. The way to do that is by meeting with them often and by having transparent conversations to see if there is mutual alignment.

“I tend to meet 2 or 3 investors every week year in, year out. No matter whether I’m at the beginning of my milestones or in the midst of it, raising capital not raising capital, but mostly just to make sure that you’re aware of who I am, what I’m about to solve and where I am at in this particular milestone, and what I might be looking for so that if we do partner one day, we know each other well enough. As you do that, what you’re indivertibly doing is placing yourself in an environment that exposes you to stakeholders that will help equip you with the right tools to execute on opportunities that arise.”


Continuous exposure to a set of people, the M&A opportunities assemble themselves.

Ed Bryant