“Everyone excellent at their craft starts from a place of deep insecurity,” says Flexport’s founding CRO Ben Braverman. People are “slow-burning fireworks,” he explains, and we need time to learn how to do anything well. If you lie to yourself, you won’t ever improve; but if you admit the truth and approach people who know more with genuine curiosity and enthusiasm, Ben says, you’ll be able to level up faster and do things you never could before.
In this episode, Ben and Joubin discuss giving speeches without prep, soliciting negative feedback, genuine curiosity, dropping out of college, valuing your experience, embracing Buddhism, outside dogs vs. inside dogs, hiring with enthusiasm, “Goldilocks companies,” the secondary sales paradox, the value of exercise, building an outbound sales machine, “natural” sellers vs. fast learners, and the warning signs that 2021 venture funding was “off.”
In this episode, we cover:
- Being yourself and the pressure to be someone else in business (08:23)
- What Flexport does and how it cracked a low-tech industry (15:36)
- The advice Ben would give to his younger self: Enjoy the ride (21:09)
- How he became the founding CRO of Flexport (26:43)
- Turning on sales and hiring Justin Schafer (31:25)
- Growing from thousands in revenue to $3.3 billion (36:59)
- The trade-offs of always being on the road (40:41)
- Personal growth in the face of exponential product growth (45:30)
- Product-led growth and the magic of list construction (50:36)
- The unique way Flexport sales managers earn equity (53:29)
- How to spot the next Ben Braverman (57:26)
- The connection between excellence and insecurity (01:03:00)
- Going from operating to investing and the long window of venture (01:05:43)
- How and why both Ben and Flexport’s founding CEO Ryan Petersen stepped aside and passed the baton (01:12:08)
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