I met Cory Janssen a few months ago and immediately knew that I needed to have him on the show. He Co-Founded Investopedia in 1999 and sold it to Forbes in 2007.
All of our recent episodes have been rather technical and sophisticated.
I felt it was a good time to share a more ‘human’ story, diving into Cory’s experience as an exited founder who eventually launched a startup studio based in Canada.
We hear it all the time; “I’m an exited founder. Now I’m going to launch a startup studio.”
But, the real question is, should you?
As an exited entrepreneur blessed with newfound financial freedom, escaping the rollercoaster of startup life probably sounds pretty exciting. However, after the initial euphoria fades, many exited founders struggle to fill the purpose void left behind.
Cory Janssen, former Co-Founder of Investopedia and current Co-CEO of Canadian-based AI venture studio AltaML, joined us to share his journey in the years following selling Investopedia to ultimately launching AltaML. He shares his hard-earned perspective on the studio model's profound challenges that demand eyes-wide-open commitment.
This episode distills Cory’s insights from an exhilarating early exit, to depressive wandering, to ultimately the invigorating but tricky process of constructing a studio specializing in building and funding AI ventures. For fellow exited founders debating their own encore, he spotlights critical considerations around mentality, partnerships, fundraising, expertise and founder relationships warranting reflection before taking the venture studio plunge.
The following is a brief summary of the personal conversation that we held with Cory. We hope you enjoy this week’s episode.
When Cory sold Investopedia to Forbes in 2008 after reaching profitability, he anticipated feeling on top of the world having achieved the liquidity that eluded most entrepreneurs. However, he descended into a serious multi-year funk only relieved by stumbling into his next challenge.
Cory reflects, “I was more depressed and more unhappy than any other point in my life...I couldn’t figure out what the next step was.”
He cautions other exited founders to avoid this drift by consciously identifying their preferred rhythm for the next season – hands-off angel investing, project-based advising, family time or plunging back into operating roles. Otherwise they risk deflating their hard-won freedom.
Specifically on launching studios, Janssen suggests, “If you need a bit of a break and you don't want to be operational, do not start a studio.” Clarity of personal readiness steers the best post-success course.
After Finally rediscovering his purpose in 2015 by building AI solutions, Cory incrementally edged into the studio model through corporate partnerships, balance sheet investing and seasoned entrepreneur backing. However, when he moved to formalize AltaML as a standalone studio with an attached venture fund, he encountered a few frustrating predicaments that are all too common.
Cory admits, “It’s brutal. It’s been absolutely brutal...You think, okay, I'm a great founder. I've raised money for my existing business (but) raising for the studio and that investment vehicle - it's a totally different beast.”
He recounts family offices dismissing his studio track record as irrelevant. VC’s passed due to his limited investing history and emerging manager status which they perceive as blind trust regardless of operating success.
To ease this fundraising friction, Cory advocates partnering with ex-VCs who have investing gravitas and credentials. He concludes, “If you can find that relationship, if you have someone that you trust to be able to start it, I think that would be probably the best thing.” Shared GP status conveys maturity that skeptical capital providers doubt in first-time studio backers.
Given Cory built Investopedia across silos like product, marketing and tech, he figured his generalist abilities would enable running a studio attacking disparate verticals. However, initial attempts exposed pitfalls pursuing this breadth without depth, spreading efforts thin. He recalls early digital media investments as “marginal” successes that sought inefficiently replicating websites despite platform advantages.
Pivoting AltaML to exclusively focus on AI opportunities transformed traction through concentrating experience. Janssen eliminated the necessity of constantly explaining elementary concepts around his specialty. He spotlights, “If you’ve got an edge and you can have a repeatable process to continually make these early stage (niche) bets, that should be an element of every institutional's portfolio.” Thus narrowing to AI enhanced fundraising and internal leadership.
Perhaps inevitably given Cory’s many years as an expert operator, Cory admits struggling not to overstep early on when working with the founders of his portfolio companies. He reflects, “Often you know that you could jump in and do a better job than the founders. But if you jump in and you do it once and you go over a founder’s head, you completely destroy trust.” This failure to foster independence proved costly.
Cory has nurtured more productive studio relationships by upholding aligned incentives. He channels the mindset, “I’m an asset at their disposal...I don’t make any money until they make money.” Studio involvement only occurs at a founder’s discretion as true peer partnerships rather than paternalism. Cory suggests openness allows teams to self-determine while benefiting from support, likening the posture to that of a consultant.
