From Welfare to Millionaire

Why Investors Should Take A Close Look At Founders With Challenging Backgrounds Who Are Making Big Waves

“Don’t worry about falling down; worry about getting back up,” I said to my teenage son this morning after he expressed his fear over performing his piano composition in front of an audience for his final class project.

The ability to get back up – or having grit – is one of the most compelling indicators of the potential for success. I am a self-proclaimed expert at getting back up and though I can’t say that I’m proud of every mistake I’ve made over the years, I can undeniably say that I am one of the most gritty and strategic people one will ever meet.

I have read that Y Combinator doesn’t invest in startups, they invest in people. So how does someone go about convincing investors and accelerators that they are the right people to invest in? Perhaps a look at the personal is not too out of line – even if the personal has been a bit challenging.

The following are some of my gritty life happenings that have helped make me the person I am today:

1. DO YOU GO ABOVE & BEYOND? I got my first job at age 12 delivering newspapers by bike. Since I had to collect payment each month, I remember very vividly that people were giving me tips and telling me that I was the only courier who had ever delivered the paper to their doorstep.

2. DO YOU SLIGHTLY BREAK THE RULES? I got my first office job at age 13 before I was even legally eligible for a minor work permit. I knew I looked older than my age and managed to “play adult” long enough so that by the time they asked me how old I was, I was 14 and their number 1 sales rep.

3. ARE YOU OBSESSED WITH LEARNING? When I was 14, I would ride my bike 20+ miles to downtown Santa Cruz where I would roam the courthouse, post office, and other public places so I could read the pamphlets they had on the wall teaching everything from tax filing to self breast exams.

4. CAN YOU FIGURE IT OUT? I’m not proud of this one because it really scared my mother, but when I was 15, I figured out how get from the Bay Area to Georgia on a Greyhound. This is before Google maps, cell phones, and the internet being everywhere.

5. CAN YOU RISE TO THE OCCASION? I got pregnant with my eldest son when I was 16. I knew that the rebellious teenager in me was going to immediately have to take a backseat to this new responsibility. He is now 16 and is quite a testament to my success as a mother.

6. CAN YOU DO WHAT EVERYONE ELSE TELLS YOU IS IMPOSSIBLE? At 17, pregnant, and behind on my credits, I was told that I wouldn’t graduate high school on time. I wasn’t willing to accept that answer so I simultaneously enrolled in college full-time and successfully walked down the graduation isle with my 2 week old son in the audience.

7. ARE YOU DETERMINED TO MAKE PEOPLE PROUD? At 18, I got a job selling software QA services (at the time, I had no clue what this meant). I booked my boss more sales appointments he could handle and he nickname me the “Golden Child of Telemarketing.”

8. ARE YOU RESOURCEFUL? At 19 and in the Bay Area, I was broke and living in a cockroach infested apartment. I learned of an affordable housing complex that was about to open, stood in line for three hours during the first day of applications, and used my quick thinking to get around some income guidelines that would have kept me out. I ended up with the last brand new 2-bedroom apartment.

9. ARE YOU A HIGH PERFORMER? When I was 20, I got what I consider to be my breakout role in sales at a startup in the Bay. After a month, I was promoted, was consistently 1 or 2 in sales competitions, and simultaneously held the record for most deals closed in company history and highest grossing deal.

10. DO YOU SUCCEED WHERE OTHERS FAIL? At 22, I got another inside sales job where my boss told me that 5 other highly skilled and technical sales reps had failed before me. I succeeded and eventually had a small team working for me there.

11. ARE YOU WILLING TO TEMPORARILY SUFFER FOR SUCCESS? After a short stint in the Central Valley in CA, I moved back to San Jose and got a job on the peninsula. I had to wake up at 5, leave my kids with a friend, walk to the light rail, take that to the train, and then take that to a shuttle which eventually got me to my job. I was incredibly broke and poor in spirit, but I showed up every single day.

12. CAN YOU SURVIVE AFTER LOSING EVERYTHING? Because of a turn of events that are beyond the scope of this article, I showed up in Seattle in 2014 with no money, two kids, and nothing but the possessions that could fit into my car. Within a month, I had two jobs and lived in one of the most prestigious high-rises in downtown Seattle.

13. DO OTHERS SUCCEED BECAUSE OF YOUR EFFORTS? One of those jobs was at Zillow, where I was number one on my team out of 18 reps for every single month of employment except one. I re-wrote the entire sales process for my team and the team average went up from about 60% of quota to about 120% of quota. My last month there, I hit 357% of quota.

14. ARE YOU TRANSPARENT ABOUT YOUR WEAKNESSES? My blog is full of tales of my struggles. This may turn some people off, but if you are going to be plopping down your hard-earned cash on a founder, don’t you want to know that they can admit what they don’t know and where they’ve been wrong? I’ll take transparency over arrogance any day – it’s the best way to know what needs to get done before disaster strikes with no warning.

If you’re in the business of investing in startups, consider adding some of these questions to your applications process. I guarantee that you’ll uncover your superstars much faster than if you just focus on traction, revenue, or product.

Melissa Strawn

Founder & CEO, MyPeopleNow.com