Wannabe Angels
Wannabe Angels
Why I Won’t Be Angel Investing Anymore - Dennis Hegstad [Ep. 11]

Why I Won’t Be Angel Investing Anymore - Dennis Hegstad [Ep. 11]

An Angel Portfolio Review with Dennis Hegstad

In this episode, Harry and Colin are joined by Dennis Hegstad. Dennis is an angel investor and the founder of Vigilance. The company protects direct-to-consumer brands from coupon leaks. Before that, he co-founded Live Recover, which was later acquired. Dennis is an expert in the Shopify ecosystem and all things DTC. He invests through his aptly named business Fake VC.

We go into Dennis’s portfolio performance originally documented in this tweet:


We discuss how he thinks about angel investing in the future and why he might be doing less of it. Welcome to the anti-episode!

Where to Listen and Watch:

Apple -

Spotify -

YouTube -


0:00 - Intro

2:55 - Dennis’ Angel Investing Journey

6:52 - Dennis Tweet

9:38 - What were Dennis’ expectations in the first angel investment?

11:57 - Angel Investing:  Helping vs. Business Opportunity  

14:28 - Lessons learned: Direct vs. Syndicates investments 

22:59 - Will Dennis continue more syndications in the Shopify Space?

27:53 - Twitter Thread - Comparing Great VCs to Good VCs and Bad VCs.

31:11 - Twitter Thread - Should raising money from investors be celebrated?

Links to Additional Info:

Dennis Hegstad LinkedIn - https://www.linkedin.com/in/dennishegstad/

Dennis Hegstad Twitter - https://twitter.com/dennishegstad/

Websites -




Aaron Harris Tweet -


Sieva Kozinsky Tweet -


Other Ways to Connect with Wannabe Angels:

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About Colin:

Colin Gardiner has spent over a decade building startups focusing on online marketplaces. Most recently, he worked for Outdoorsy as Chief Revenue Officer. He advises marketplace/platform startups on growth, analytics, monetization, fundraising, and strategy. He also runs the rapidly growing syndicate Yonder Ventures, which invests in marketplaces and platforms and the SaaS, Fintech, Insurtech, and the technology enabling them.

Colin LinkedIn - https://www.linkedin.com/in/colingardiner/

Colin Twitter - https://twitter.com/ColinGardiner

About Harry:

Harry Campbell runs The Rideshare Guy, a popular community for drivers and gig workers in the rideshare and delivery space. He’s an active angel investor, having invested over $500k in 30+ companies and funds over the past few years; he is still trying to figure it all out, though!

Harry LinkedIn - https://www.linkedin.com/in/harrygcampbell/

Harry Twitter - https://twitter.com/TheRideshareGuy

Wannabe Angels
Wannabe Angels
We are the angel investing JV team, and we are interviewing and learning from the best angel investors around.