Life as an Entrepreneur: Expectations vs. Reality

We’ve all had a vision so clear and perfect we can almost feel the tug of the finish line ribbon, only to have our expectations fall into a million pieces for us to pick up. To Jessica Mah, that vision was to be an entrepreneur. Leading a company is something she always knew she would do. But that certainly didn’t end up the way she expected at 8, 11, 19, or 21 years old…

In this interview with Silicon Valley legend Steve Blank (recording below), Jessica reveals what it was like growing up with deep entrepreneurial drive coursing through her veins from adolescence to adulthood. Here she reveals how struggling to find a place as a student vs. a full-time business owner in her early life helped frame Jessica’s mindset that would ultimately spawn her disruption in the accounting industry. From there, the two entrepreneurial minds dive into the deeper reasons indinero 1.0 came so close to sinking completely and what she learned over her hands-on journey bringing it back to life.

About Steve:

Steve Blank is regarded as a pioneer of the entrepreneurial mecca that is Silicon Valley and his Customer Development methodology is credited as the origin of the Lean Startup movement. Steve has since switched gears from entrepreneur to educator as a lecturer at top universities (Stanford, and UC Berkeley, to name a couple), and the host of his own SeriusXM radio show, Entrepreneurs are Everywhere.

Listen to Steve and Jessica’s full interview here:

(Skip ahead to key points and takeaways using the time stamps listed below)

Use these timestamps to jump to key topics Jessica and Steve covered:

00:00 – Intros + Jessica’s early life: Addicted to entrepreneurship at an early age. Steve: “Is precocious a word to describe you?”

03:18 – High School Education & College Life. Jessica: “I was in all honors classes and managed to get kicked out of all of them… You have to be a little crazy to drop out of high school to go to college”

05:19 – Steve: “What did the ‘path to success’ mean for you? What do you think it means now?”

06:45 – Questioning everything & challenging authority. Jessica: “I didn’t think I’d make a good employee, I knew I wanted to be an entrepreneur… I thought it would be a lot more glamorous than it actually is.”

07:40 – Solving a real problem that no one wanted to fix: Accounting as the road block for early business. Jessica: “[in high school] my accounting was a nightmare, my cash flow was mismanaged, and that’s what led us to not be able to finance the company and grow…”

Reading Break: Jessica Mah’s “6 Things I Did to Build One of the Country’s Fastest-Growing Companies”

10:30 – How Y Combinator helped indinero. Jessica: “I still keep in touch with many of the I met from the program”

11:09 – Getting good press, lots of money, and totally ahead of ourselves. Jessica: “I don’t read any of the press. I don’t want this stuff to get to my head whether it’s good or bad.” Steve: “It’s really easy to get caught up in your reality distortion…”

12:37 – Retiring at 25, or not: The first big surprise. Jessica: “Well, I’m 25 and that’s still not the case…”

13:18 – An expensive and important lesson about losing friends. Steve: “Being boss to your friends is being different than friends to your friends…”

15:17 – Burning a $700,000 hole in our pockets. Jessica: “I was really freaking scared, Steve!”

16:42 – Bad Omen: Hot tubs in the office. Steve: “You did something fascinating, cut your cash burn down until you could figure out what to do.”

18:10 – Reconfiguring out the path to success. Jessica: “What kind of painkiller offering can we build?”

19:00 – Product Marketing in raw form: Working backward to find the painkiller product. Jessica: “We did a Stanford though leaders interview right in the thick of the storm”

19:37 – Partnering better, smarter tools with real humans. Steve: “So, a customer actually taught you what you needed to do?”

22:55 – Substituting job experience with self-development. Steve: “You didn’t have the apprenticeship experience of working for other companies/startups … is that what you mean about talking to other entrepreneurs?”

24:22 – What Jessica Mah wishes she’d known about investors. Steve: “Meaning there’s a good time to raise money and bad times?”

25:14 – Final thoughts. Jessica: “Regret is a strong word, but yeah I have regrets…”

Recommended Reading: “How Software Automation Is Unleashing Talented Bookkeepers” (Blog Post)

This interview was originally shared on Steve’s blog post on