Embracing Entrepreneurship at 35

By Rena Thiagarajan, 2-4-2014

When I was 22, I was working as an entry-level engineer on offshore oil rigs in the Gulf of Mexico. When Evan Spiegal was 22, he was building a company (Snapchat) that would go on to be valued at an estimated $3 billion or more.

There’s no shortage of headlines these days about millennials like Spiegal, in hoodies, making millions in Silicon Valley. Yet — fortunately for the rest of us — data also shows that there’s a strong correlation with older age and success as an entrepreneur. For example, Jan Koum was 33 and Brian Acton was 38 when they founded WhatsApp. Both men, like me, had spent most of their twenties as salaried employees of large companies before launching their own company (the hugely successful messaging app that sold to Facebook for $19 billion).

I founded my first company, Project Bly, last year at 35 — 13 years after my first engineering gig. Unlike Spiegal, I had over a decade of work and life experiences before I went out on my own. After working at as an engineer for a year, I pursued a more traditional career path and did what a lot of smart, ambitious twenty-somethings not starting companies do: I applied to law school. After graduating, I learned the ins and outs of corporate law at a big firm in Silicon Valley and eventually became general counsel at a clean technology company.

I spent almost seven years lawyering, and while I worked hard and did well, I rarely woke up excited to go to work. As I approached 35, the realization that how I spend my days is how I will spend my life hit me. I wanted to stop living in anticipation of more fulfilling, happier days, but wasn’t sure if I could step off a carefully laid career path to chase a dream. The answer I needed came during a trip to India, where I spent hours exploring the city’s chaotic and vibrant street markets.

Project Bly had been just an idea for years. The first seed was planted when I spent several months looking for a one-of-a-kind rug with history and story. It grew after a trip to Sao Paulo where my online research for the best flea markets and street art resulted in over 20 open tabs. And then it all came together on the streets of Mumbai: I wondered, why weren’t there any travel sites focused on street culture? Weeks later, I sat down and wrote a business plan for a travel and design website built on the philosophy that to really know a city, you must wander its streets.

Project Bly was built in San Francisco coffee shops, filled with other entrepreneurs huddled over their Macs — all more than a decade younger than me. Intimidating? Maybe at first, but once I actually started building my company, I realized that 35 is a great age to take the leap to entrepreneurship. Here’s why.

1. I’ve worked with all types of people. With over a decade of work experience, I’ve had to work with different kinds of people and personalities. I’ve worked with difficult people, as well as people whom I admired and respected, people who inspired me and others who advised and mentored me. I’ve worked for the boss who gave me more responsibility than I wanted, but I rose to the occasion and made him proud. On the other hand, I’ve also had the boss who micromanaged and belittled me. These experiences have taught me not only how to get along and work as a team despite potential personality conflicts, but also what kind of leader I want to be with my own team — and what kind of leader I don’t want to be.

2. I’ve got perspective. Much like being thrown together with different kinds of people, having worked in different companies has given me invaluable perspective on the kind of company I want to build. I’ve experienced how demotivating hierarchy can be and seen layoffs go badly. I understand that company culture is more than a foosball table and free food; it’s about creating an environment where intangible values like respect, honesty and kindness are always in the forefront.

3. I’ve got the confidence to learn what I don’t know. I’ve learned over the years that I will not know how to do everything, but what I don’t know, I can learn. I didn’t have an engineering degree when I applied to my first job, but once I got it, I learned what I needed to. Being thrown into the deep end is one of the best ways to learn, and knowing I’ve swam before has given me the confidence to keep going. From design to accounting, I’ve taught myself what I need to know to run my company, including learning enough to put together an extremely smart and talented team.

4. I’ve got money in the bank. One of the big advantages of being older is that I had money in the bank to start Project Bly. As a lawyer making a six-figure salary, I saved consistently and invested wisely, and used my savings to start Project Bly. While it doesn’t make the road ahead any easier, having savings meant that I could get off the ground and build a product before needing to raise money from outside investors. Project Bly is still bootstrapped and I wouldn’t have gotten this far if I hadn’t worked hard and saved.

5. I’ve got a network. At 35, I have wide social and professional networks. I made several enduring relationships and friends from graduate school and prior jobs. These friends and past colleagues were the ones I reached out to, not only to raise seed money for Project Bly, but also for advice. For example, the old CFO from my last job helped me set up my Chart of Accounts on Quickbooks, and one of my law school classmates is an investor.

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