Failure Stories Volume 3
Gina Gotthilf co-founder of Latitud and former VP Growth at Duolingo shares lessons from big vs. small companies and fear of losing her visa
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Welcome to the third installment of Failure Stories. You can find the first volume with Elena Verna and Leah Tharin here and the second volume with Tom Willerer here. I try to share one of these every month.
Failure. We’ve all experienced it but hate to talk about it. And why is that? As leaders, are we supposed to be flawless; impervious to criticism and mistakes?
Are we worried that if our teammates, peers, bosses or direct reports find out about some huge flop our ours that we will somehow be less successful than we were a week or two ago or that it might hold us back from that future career opportunity?
In Product we prototype because we know that on a great day only 30% of our solutions will actually work. In Growth we experiment for the same reason. Even the smartest and most talented among us get it wrong, have moments of immaturity, and learn some painful lessons.
The party line is that failure is “OK” because it’s about learning. But, when it comes down to it, is it really okay to fail?
Yes. It is. And because it’s so hard to admit failures I’m publishing this recurring series on the stories of some of the most successful leaders and the struggles along their journey to success. My hope is that this normalizes the losses and mistakes that we’ve all experienced but are too afraid to share. The ones that make us deeply uncomfortable and are a big part of what has forged the successful people you follow today. Those whose advice you clip and save for later, whose newsletters you subscribe to, and whose templates you share.
With each person I ask them two questions:
What would you consider to be the biggest professional failure of your career – what’s the story behind it and why was it such a big flop?
How did that experience shape you; how did you transform it into a learning opportunity?
Today I’m sharing two great stories from Gina Gotthilf – COO and co-founder of Latitud, former VP of Marketing & Growth at Duolingo, the subject of a First Round Review article and a fantastic interview on the 20VC podcast. Gina is an incredibly successful founder and executive, but along the way she’s had some bumps in the road, some tears, and anxiety-inducing decisions. She shared these with me candidly and her biggest lessons learned.
“I had a pretty rough beginning to my career including having a lot of trouble finding my first job, getting laid off and then later fired — all of which were exacerbated by the fact that I needed a work visa to maintain my life in the US.”
Story 1: Finding places you’re valued
The earlier part of Gina’s career was marked by working at several companies where she wasn’t really valued and her employment fell apart.
She recounts these stories:
“Every day was an uphill battle and especially in the beginning of my career. I shed many tears in the office bathroom wondering if I was worthy of a career or doomed.”
The last straw was joining a Digital Ad Agency called Attention–it was the third marketing agency she worked for and she lasted 10 months. She vowed never to work for a marketing agency again.
The earlier part of her career looked like this:
Newspaper Editor: ~1.5 years
Research: ~1 year
Social Media Strategist: ~1 year
Social Media Strategist: ~11 months
Digital Marketing Manager: ~10 months
These short stints had Gina struggling to get out of bed in the morning and wondering if she could survive and build a lasting career or if something was wrong with her. She struggled to find value and feel valuable.
Shortly after each of those experiences, just as she was losing hope, she’d have an amazing experience.
“However, shortly after those experiences, I’ve had roles where I absolutely thrived even though I was the same person with the same skills set.”
How did that experience shape you; how did you transform it into a learning opportunity?
“My lesson: it’s important to find a job where you can work with people you admire and they value you. If it’s not your current job, try again.”
Since those early experiences Gina has gone on to a 5+ year stay at Duolingo, joined a board, worked for a US presidential campaign and raised millions of dollars for her startup, Latitud which supports early-stage entrepreneurs in Latin America.
Not a bad second act for someone who doubted their own worth early in their career.
Story 2: Making the “safer” choice
Oftentimes we think that the better and safer choice is the one at a larger company. It seems more stable, more predictable, and overall more secure. Gina had an additional reason for seeking out this safe choice: visa sponsorship.
She had two job offers – an earlier-stage company and a later-stage one.
“The second failure I think of to this day was a moment in my career when I chose a more established company over a startup because I thought it was a safer choice. The fear of not getting sponsored for the visa propelled this decision.”
It turned out though that bigger doesn’t always mean safer. And Gina’s biggest fear in joining the smaller company was realized at the bigger one.
“It was in fact not safe at all — I was fired 8 months later and had to return home to Brazil. And it's actually worse -- I told the startup I'd work for them and then backtracked.”
How did that experience shape you; how did you transform it into a learning opportunity?
Gina took away two large lessons from both of these experiences.
First,
“Finding people you admire who value you as a professional can be more important than how established a company seems.”
And second,
“Always do the right thing — I'm still ashamed I said yes [to that small startup] and backtracked on my word, and think about it to this day.”
Conclusions and takeaways
I appreciate Gina’s vulnerability and honesty in sharing these stories with me and you. I came away with a few thoughts of my own:
Fear is a powerful, but challenging motivator. Gina was afraid, rightfully so, of losing her job and having to leave the United States. That fear was so strong it caused her to put blinders on to other decision criteria involved in company selection. And those other factors ultimately led to her losing her job and having to leave anyway.
Find people you admire who value you. These are definitely not the same thing. There are plenty of admirable people and leaders out there who are terrible human beings. Make sure you vet them well in your job search. That means reverse interviewing and understanding the values you want a company and its people to live by.
Your career has multiple acts. Gina had six jobs in fewer than 6 years. She doubted herself and her abilities. She found herself crying in the bathroom. And then… she took Duolingo on an impressive, 5+ year run, worked on a US presidential campaign, had First Round Review articles written by her, met the President of the United States, co-founded a company and did this amazing interview on 20VC. If a company can pivot so can a person. It’s all about finding your own, personal PMF.
If YOU have a failure story that you’d like to share or any feedback on this series please reply and let me know.
I've had those same experiences as Gina, almost to a T, so this hit me right in the feels. If I had this post back then, I know past me would have appreciated knowing that things would turn around - so please keep writing them!