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David Adams, Founder and CEO of Sniffspot

May 29, 2019

What were you doing before you quit your job?

I quit my job twice. The first time I was a strategy manager at Microsoft on the Xbox team. The second time I was running the marketplace at Crowd Cow.

When did you realize you wanted to quit your job?

After I had been at Microsoft for 3 years, I started to feel like it was time to try something new unless I wanted to stay at Microsoft forever. I also applied for business school at Stanford on a whim and was accepted. So I felt like that could be the perfect hedge for exploring a startup without risking losing career momentum.

The second time around it was a lot less anxiety inducing. I feel like a career is much less of a track now (I think the world has changed toward this direction recently). I was happy with a side gig, Sniffspot, around the job at Crowd Cow, but then I got an offer for funding for Sniffspot and I decided it was worth it to try again!

What initial hesitations did you have about quitting your job and how did you overcome them?

The first time it was a torturous decision. I really liked my job and my team and had good career prospects. I was also terrified of “losing career momentum” by leaving an established job. However, I was also haunted by the possibilities. What was I leaving on the table by not trying my hand at a startup that has unlimited upside?

Can you remember the day you put in your notice? What was it like, what was going through your mind, how did your manager take it?

I was very close with my manager. He knew I had applied to business school and wrote one of my references. When I told him he put together a pretty compelling counter offer and it made the choice that much harder!

What are you doing now?

Now I am working on my second startup, Sniffspot! I am really excited about applying all I learned from my first startup to Sniffspot, including how I vetted the idea and how I am building the company.

Looking back on your experience of founding a company, what do you know now that you wish you knew before? Are you happy with your decision?

I don’t think there is any way to know if being an entrepreneur is right for you until you try it. For me, it’s a perfect fit. It’s hard to have any advice about how I went about it, since every startup is very contextual and personal. I would recommend trying it. The only time better than today is yesterday.

Any other advice you can share for others contemplating a similar path?

If you have interest in it, try it to find out!

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Will Gordon, Co-founder and COO of Latchel

May 27, 2019

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What were you doing before you quit your job?

I was leading a part of the Amazon Worldwide Last Mile Subject Matter Expert team focused on on-road planning and execution (I.e. Route planning, tracking, and delivery devices and software)

When did you realize you wanted to quit your job?

My family needed help with managing their rental properties. After spending some time helping out I realized the maintenance tracking problem space had surprising parallels with last mile delivery.

What initial hesitations did you have about quitting your job and how did you overcome them?

I really enjoyed working at Amazon, but had always had a goal of building my own company. I felt it was now or never, since my vesting schedule would only make it harder and harder to leave. I figured it was better to bite the bullet and stop vesting before it got too hard to resist.

Can you remember the day you put in your notice? What was it like, what was going through your mind, how did your manager take it?

I don’t remember much other than the conference room had a round table and my manager was disappointed I was leaving but understood the impulse to be an entrepreneur.

What are you doing now?

Latchel offers 24/7 maintenance for property managers. I’m COO and am focused on building better operations processes and transparency.

Looking back on your experience of founding a company, what do you know now that you wish you knew before? Are you happy with your decision?

I wish I knew how important it is to achieve product market fit (and what product market fit really meant) before trying to grow aggressive. It’s hard to grow your customer base when you have significant customer churn. We tried to expand sales too early because we had strong demand, but we didn’t realize our product was a leaky bucket at the time. If we knew this at the beginning we could have extended our runway substantially before fundraising again.

Any other advice you can share for others contemplating a similar path?

Pick a problem space or a customer base you love. The lows get really low so you need something to hold onto to get you through them.

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