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The Mistake I Made at Uber That Taught Me Everything About Sales
Most founders and fractional executives struggle with sales — not because they lack skills, but because they're leading with the wrong message. Bradley Jacobs breaks down how he learned this the hard way, sharing stories from his time at Uber that fundamentally shaped his approach to selling.
It started with a rejection. After a successful Uber Eats launch in Miami, Bradley was turned down for a GM role and kept hitting walls when pitching for other positions internally. The problem? He was making it all about himself. The shift came when he reframed his pitch around what the company actually needed — launch expertise for a global Uber Eats rollout — and suddenly got a one-way ticket to Amsterdam.
That mindset carried into his first consulting engagement, where he landed a $25K/month fractional role with a Series A startup by focusing entirely on their problem, not his credentials. No hard sell. Just a clear solution to a high-stakes challenge they were already facing.
Bradley connects these lessons to content strategy and LinkedIn, arguing that value-first content works the same way: give generously, ask strategically, and when you do ask, make the ask itself a value exchange. The formula is simple — solve real problems, ask good questions, and share everything you know.
Learn More:
Elevate your voice: https://mylance.co
Connect with Bradley Jacobs: https://www.linkedin.com/in/bradley-r-jacobs/
00:00 Introduction and Mylance overview
00:34 Learning to sell through mistakes
00:56 The Uber Eats Miami launch story
01:45 Hitting walls with internal pitches
02:46 Lesson 1: Make it about them, not you
03:41 Reframing the pitch around Uber's goals
04:35 Getting the yes — a ticket to Amsterdam
05:24 Fast forward: going fractional after Uber
06:02 Reaching out to 12 companies cold
06:44 Finding the problem worth solving
07:19 Building the $25K/month proposal
07:56 Landing the first consulting client
08:50 Three core lessons from that win
09:41 How content works like a proposal
10:28 Sharing mistakes as value-add content
11:01 One takeaway: always add value
12:15 The give/give/give, then ask model
12:37 How good questions create value
13:41 Value-first content strategy explained
14:17 The 90/10 rule: give vs. ask
15:07 Summary and closing thoughts
15:36 Check out Mylance
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By Mylance
5
77 ratings
Most founders and fractional executives struggle with sales — not because they lack skills, but because they're leading with the wrong message. Bradley Jacobs breaks down how he learned this the hard way, sharing stories from his time at Uber that fundamentally shaped his approach to selling.
It started with a rejection. After a successful Uber Eats launch in Miami, Bradley was turned down for a GM role and kept hitting walls when pitching for other positions internally. The problem? He was making it all about himself. The shift came when he reframed his pitch around what the company actually needed — launch expertise for a global Uber Eats rollout — and suddenly got a one-way ticket to Amsterdam.
That mindset carried into his first consulting engagement, where he landed a $25K/month fractional role with a Series A startup by focusing entirely on their problem, not his credentials. No hard sell. Just a clear solution to a high-stakes challenge they were already facing.
Bradley connects these lessons to content strategy and LinkedIn, arguing that value-first content works the same way: give generously, ask strategically, and when you do ask, make the ask itself a value exchange. The formula is simple — solve real problems, ask good questions, and share everything you know.
Learn More:
Elevate your voice: https://mylance.co
Connect with Bradley Jacobs: https://www.linkedin.com/in/bradley-r-jacobs/
00:00 Introduction and Mylance overview
00:34 Learning to sell through mistakes
00:56 The Uber Eats Miami launch story
01:45 Hitting walls with internal pitches
02:46 Lesson 1: Make it about them, not you
03:41 Reframing the pitch around Uber's goals
04:35 Getting the yes — a ticket to Amsterdam
05:24 Fast forward: going fractional after Uber
06:02 Reaching out to 12 companies cold
06:44 Finding the problem worth solving
07:19 Building the $25K/month proposal
07:56 Landing the first consulting client
08:50 Three core lessons from that win
09:41 How content works like a proposal
10:28 Sharing mistakes as value-add content
11:01 One takeaway: always add value
12:15 The give/give/give, then ask model
12:37 How good questions create value
13:41 Value-first content strategy explained
14:17 The 90/10 rule: give vs. ask
15:07 Summary and closing thoughts
15:36 Check out Mylance