WHAT WERE YOU DOING BEFORE YOU VENTURED OUT?

Before I quit my job, I was CTO of CarRentals.com, part of the Expedia Group.

WHEN DID YOU REALIZE YOU WANTED TO VENTURE OUT?

About a year and a half before I left, I realized I was ready to do something different. I started my search “the traditional way” for someone who had worked in large companies - looking at roles at the likes of Amazon, Google, and Microsoft. But I couldn’t find anything that reignited my passion. At the same time, I was getting more involved as an advisor for a local startup founded by an ex-coworker. Following their journey, I realized the diversity of experiences in a startup would give me the strategic and technical challenges I was looking for. I wanted the thrill of knowing what I did mattered and realized the risks of a startup were exactly the draws I was looking for to let me live more.

WHAT INITIAL HESITATIONS DID YOU HAVE ABOUT QUITTING YOUR JOB AND HOW DID YOU OVERCOME THEM?

Like many I was worried about the financial impact of leaving my job but decided to test living without an income by diverting my paycheck to another account. This let me see how much I could cut back and exactly how much I needed to supplement. The great part about this was when I did quit, I had built up enough from redirecting my paycheck that I’m now able to “pay” myself what I need to get by, and know what that personal runway looks like.

Another hesitation I had was whether I’d be able to live up to the pace and expectations of a technical co-founder with limited help, especially as I had only worked in large company roles before. I was able to alleviate this concern through hands-on work with some early-stage companies that let me build up their technology stacks. This gave me reassurance that I was ready to take on this role full-time.

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 fortunate to have a great manager at Expedia, and he knew I was itching for something different. I had been talking with him about several opportunities I was considering in the months leading up to my departure. So it was a bit anticlimactic when I told my manager I was leaving; he knew it was coming. My team, on the other hand, was quite surprised but supportive of my move.

WHAT ARE YOU DOING NOW?

I’m now the CTO and co-founder of LegUp, focused on using technology to help working families find trusted child care on their journey from pre-birth to the pre-teen years.

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 knew that the pace would be different and the priorities unclear compared to a large company role. I didn’t really appreciate though how fast things would move and how many trade-offs I’d have to make on a daily basis. It’s invigorating and what I was looking for, so I’m definitely happy with my decision, but it’s been a learning curve no doubt.

ANY OTHER ADVICE YOU CAN SHARE FOR OTHERS CONTEMPLATING A SIMILAR PATH?

It’s really important to know what you’re looking for and why you want to venture out. It’s different for everyone. For me, it was looking to take more risk and live more. After some coaching and much retrospection, I boiled it down to “the three P’s”: Personal Relationship (with other cofounders), Potential (positive impact for the world and personal payout), and Passion (a sense of excitement and enthusiasm around the space). With this framework in mind, I was clearly able to assess different opportunities until I found a great opportunity with LegUp!

For more information on LegUp, please visit www.legup.care.

What were you doing before you ventured out?

Before I quit my job, I was a founding partner of a company called Studio216.  Studio216 is an immersive technology agency based in Seattle. They create architectural visualizations and XR related content/experiences for mid-market and enterprise businesses.  I started the company in 2005 with two close friends and we ran the business together for over a decade.  

When did you realize you wanted to venture out?

In early 2017, I started to have ideas about how mobile computing was going to change.  Apple was making some noise about augmented reality and announced ARKit to the public after the global success of Pokemon Go in the AppStore.  I was determined to refocus the existing business, take advantage of mobileAR and the changes that I predicted would be happening in the e-commerce space.  I presented a business plan to my partners and they weren’t in alignment.

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

Initially, I was worried about the financial consequences of leaving a businesses that was doing well and providing an income for me and my family.  I was also unsure about my ability to raise money. My first business was bootstrapped and I had no experience fundraising. Once I left my day job and started reaching out to potential investors there were a couple thoughts that helped me through the process. 

First, I convinced myself that success was a game of numbers.  I took as many meetings as I could, understanding that it was going to take a lot of people telling me ‘No’ to get to ‘Yes’.  Focussing on the numbers game helped me take the rejection less personally.  

Secondly, I celebrated the small wins.  Even small amounts of investor and customer interest are worthy of celebration.  The singles add up to big wins. The home runs are great, but far and few between.  Celebrating the singles kept my momentum up and after two months of being in business I had closed my seed round of financing.

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?

The day I put in my notice in I was nervous.  I had to tell my partners about my decision and I knew there were going to be legal repercussions that would follow.  They were disappointed, but we were able to get through the details that led to my transition out of the company.

What are you doing now?

Currently, I am the CEO of a company called Simply Augmented.  Simply Augmented is a Seattle startup that helps businesses, that manufacturer physical products, take advantage of 3D and AR to market and sell more effectively.  We raised our seed round in 2018, have acquired our first paying customers and are in the process of preparing for our next round of financing.

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?

Looking back on the decision to leave my old company, I am ultimately happy with the decision.  I have learned so much in the last 16 months about myself and about being the leader of a team. One thing I wish that I had done more of in the early days was reach out to more potential customers and actively listening to their problems.  We often have ideas of things we think will work, but they are not based on real customer problems that we are trying to solve. I would have saved a lot of time and money if I listened more closely to customers before building product.

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

The last 16 months have been energizing, stressful, challenging and interesting.  The path forward is not without obstacles, and the road is long. Be prepared for a fight, but if you treat each day as a journey and celebrate the wins, each small step will add up to big accomplishments.

For more information on Simply Augmented, please visit www.simplyaugmented.com.

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!

For more information on Sniffspot, please visit www.sniffspot.com.

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.

For more information on Latchel, please visit www.latchel.com.

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]]>Will Gordon, Co-founder and COO of Latchel