Leaving Google to be a Startup Founder

My journey and learnings 2 years after taking the plunge

It’s been 2 years since I took the plunge to leave the best corporate job in the world to dive into the uncertainty and exhilaration of starting my own company, Sparket. A lot of people have asked me how it felt taking the plunge and why I did it. So I wrote a blog (my first ever!), in the hopes that I can share with others out there who are grappling with the same decision. I hope any of you with corporate jobs who have thought about entrepreneurship find it useful! 

Highlights

1. Dip your toe in first 

2. Trust your gut to dive all in

3. Prepare for frustration and rejection

4. Protect your mental health

5. If you approach it right, it’s worth it! 

1. Dip your toe in first

It started with Aaron and I talking about business ideas casually over beers - we'd ideate, and dream, and occasionally write a one-pager or flesh out a bit more detail. We did this for months, until an idea stuck. We found ourselves coming back to it again and again. It was in an area we were passionate about (sports and gaming), had the skills to execute on (tech and math), and in a fast growing market (sports betting). 

But, we both still had full time jobs, and couldn’t just give up our livelihoods for a cool idea. So we started building it on nights and evenings, and started tapping our network to find advisors and part-time “employees” who shared the vision and took early equity to help us. We did this all with completely independent equipment and time from our full day jobs (very important to avoid your current company having a claim on your new business!). As terrible as they were, COVID lockdowns helped us a lot in that regard, as people were at home and didn’t have much else to do. And slowly, the Social Betwork was born.

I share this to dispel the myth that I heard often early on “you need to go all in!”. No, you don’t, and sometimes it’s foolish to. There are ways to get early signs of whether your idea can be a sustainable business without fully committing to it. When you get those signs, then you can decide. 

2. Trust your gut to dive all in

I just woke up one day and felt it. After months of agonizing about if / when I would leave Google to work on Sparket full time, I simply knew it was time. Things had gotten a lot more real. We had a working beta product and our first pilot client was successful. We had secured a 6 figure investment from a strategic individual. And while it wasn’t enough to pay ourselves, it would be enough to pay the development team we needed to get our software to a launch. 

Working at Google was amazing, but I simply knew it was time. Like so many other things in life, your gut has the power to cut through thousands of incessant thoughts and guide you in the right direction. 

So I bounced it off a few loved ones to make sure I wasn’t crazy and few weeks later I walked away from $400k+ annual comp, free food, massages, and all the perks that come with a modern tech job to pursue a startup which paid nothing and had no guarantee of lasting through the year. 

3. Prepare for frustration and rejection

From the outside, being an entrepreneur can sound glamorous. I hear a lot of “I’ve always wanted to do that”, “it must be great being your own boss”, etc. And while that’s true maybe 1% of the time, the rest is an absolute slog. You have to be ready to do everything: product, sales, operations, marketing, legal documents, HR, investor pitches, management, individual work, and on and on. I used to suck at sales and had to be our salesman with Aaron so we learned how to get better at it and surrounded ourselves with the right people.

The payoff is big when you succeed, but most things you do will fail or take a long time to come to fruition. Along the way you’ll have to make very painful decisions of letting projects or team members go. That’s not to mention the lifestyle change you’ll likely have to make due to the large pay cut you’ll take personally. Being the decision maker does come with a lot of benefits and flexibility of course, but you should go into it with your eyes wide open about the implications.

Meanwhile, you need to be prepared to adjust your ego and absorb a LOT of rejection. 95% of the investors you pitch will say No. Likewise with potential clients. Your product launches will get less traction than you hope. There will be bugs, glitches, and mistakes which feel devastating. You have to be stubborn and maybe a bit crazy to keep powering through. 

4. Protect Your Mental Health

This is a big one that I didn’t fully consider when making the leap. Corporate jobs can be stressful and demanding, but ultimately, at the end of the day, you can shut the work off. With your own company, this becomes a lot more difficult - you always feel like you could or should be doing more. No matter how passionate you are about your corporate job, it won’t compare to your startup baby. Trying to take a vacation or disconnect in the evening becomes exponentially more difficult when you have so much personally invested. 

And the pressure will pile up. Not only are you personally invested, but you’ve likely taken money from friends/family. You have a team who’s taken a risk to join a small startup based on your vision, and clients you took a chance on an unproven product. When the inevitable tough times come, your mind can naturally drift towards the worst case scenarios and how you’d be letting these people down. 

So how do you protect your mental health? I could write an entire blog about that, but for me it comes down to some of the same principles that you would take to balance your work/life in a corporate job. Only now, they become more essential.

• Find a way to implement mindfulness in your life. This means something different to everyone, but to me it’s taking on the challenge of disconnecting from work. For me it needs to happen for at least 30-60 mins in the middle of the day (whether that’s a workout, a walk, a phone call with a friend, etc.) so I’m not caught staring at my computer immersed for 10 hours straight.

• Celebrate the wins! Human nature naturally emphasizes loss and mistakes, so you have to be intentional about celebrating even the small wins in your company. Share them with the world and with your team. Take a moment to appreciate the work that went into it. 

• Remind yourself of why you’re here. It’s easy in the day to day to lose sight of your vision. Even when it doesn’t feel like it, you’re living a dream in getting to pursue one of your passions! 

5. If you approach it right, it’s worth it! 

Sounds like a lot of challenges. Do I miss Google? How’s the startup doing? Was it worth it? 

For sure I miss Google. I got to solve challenging problems with some of the coolest and brightest people in the world, while eating free food and traveling the world. I will say my experience there helped me tremendously to gain a perspective of corporate life at its best, as well as some of the red tape and excessive processes to avoid.

Sparket is doing great– we’ve had ups and downs but have transformed in 2 years into one of the hottest startups in the sports betting space. We still have a long way to go but I’ve never been more bullish about our prospects. 

Despite the somewhat pessimistic tone in some of my commentary above, I would say with 100% conviction that the decision to take the plunge was worth it. You only have limited opportunities where the stars align, and if you don’t take advantage of those moments you will always wonder what could have been. If it fails or you hate it, you can always go back to your corporate job. Maybe you’ll get rich and buy an island, or make an indelible social impact on the world. 

But even if you don’t (as most won’t) you’re going to learn so much. That’s the most important part for me. I’m learning about all aspects of business in ways that will make me a better and stronger person not only in my career, but in life. 

Thanks for reading- would love to hear your comments or connect with you on LinkedIn.