Ep. 2 - From Standup Comedy to VC: Embracing Life One Opportunity at a Time - with Bob Gillespie
In this episode, we had an absolute blast chatting with Bob Gillespie, Managing Partner of REACH Commercial, the commercial fund of Second Century Ventures, and let us tell you, it's a ride you don't want to miss! Even though he’s no longer a stand-up comedian, Bob is a testament to the power of humor and public speaking when pitching new ideas and solutions. Think of it as stand-up comedy with a dash of TED Talk brilliance! For those of you in career limbo, fret not. Our guest shares golden advice on how to tackle what he calls the painful “waiting game” between professional moves. Instead of agonizing over LinkedIn notifications and making the right decision, why not learn a new skill?
And speaking of trends, if you’re wanting to know how to create a winning solution in PropTech, Bob walks us through the key of taking something that’s dumb, slow, and expensive, and turning it into something smart, fast, and cheap.
Want to hear more controversial takes from Bob? Be sure to listen to learn more! 🎧
Show Notes:
0:10: Nadine's new lifestyle and Ryan's past criminal life
7:20: Introducing Bob Gillespie
9:50: Bob's career journey
23:26: How to tackle the "waiting space"
30:18: Latest PropTech solutions
40:15: Necessary changes to real estate innovation
45:05: Bob's advice to young CRE professionals + his take on ClimateTech
53:32: Bob's move to Costa Rica
57:42: Postgame recap
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