Wannabe Angels
Wannabe Angels
Unleashing the Power of 'Go to Market' with Kyle Richless [Ep 17]

Unleashing the Power of 'Go to Market' with Kyle Richless [Ep 17]

In this episode, Colin and Harry talk with Kyle Richless. Kyle is a hands-on, GTM advisor/investor, with a particular focus towards optimizing the commercial machine of 2-sided marketplaces, verticalized SaaS plays & and consumer businesses (e.g. leveraging a capital-efficient growth marketing motion). 

The first 9 years of his career, post law school, he helped to build the commercial machine at a first generation, legal tech startup - called Axiom Law - backed by Benchmark - and which was exited to Permira (the global PE firm) in 2019.  From there, he has been an active angel, has spent time as an operating partner at 2 funds, and co-founded a biz called CapGains, which is still growing today, and which leverages tech to automate tax incentives for startups and VCs.

Where to Listen and Watch:

Apple -

Spotify -

YouTube -


0:00 - Intro

02:19 - Kyle’s angel investing experience

07:12 - “Go to market” defined

14:40 - How did Kyle go from founder to angel investor?

20:27 - Angel investing is more than an investors money

23:27 - The importance of being helpful as an angel investor

30:23 - What is an operating Partner?

33:31 - How is a scout different from an operating partner?

35:29 - Advice for becoming an operator

39:58 - What would Kyle do differently in his angel investing journey now?

41:38 - Twitter Thread - Does a VC/angel investor help in more ways than just a check?

43:49 - Tweet 2 - Is it ok for a founder and an angel investor to communicate by text?

Links to Additional Info:

Kyle Richless

LinkedIn - https://www.linkedin.com/in/kylerichless/

Twitter - https://twitter.com/KyleRichless

Website -


Zehra Tweet -


Caroline Casson Tweet -


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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!

Interested in learning about some of the companies Harry is angel investing in and read his deal memos, for FREE - just fill out this form - https://forms.gle/eYwtDE7p9K2bepnF8\

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.