1. What were you doing before you quit your job?

My previous experience was Amazon, Uber and most recently Convoy. I joined Convoy when it was roughly 30 employees, and was fortunate enough to see it grow to 1000+ over 3.5 years. When I left, I was leading the Operations org, and had an amazing team that included Operations, Customer Support, Program Management, Data Science, L&D and other functions.

2. When did you realize you wanted to quit your job?

A few people in my network had begun their own ventures – after talking with them about their experience, I started to consider entrepreneurship more deeply. I ultimately came to the decision after discussion with my family, but it was more about moving towards founding my own company then it was about quitting my job. I was afforded an incredible opportunity at Convoy, but didn’t have the time personally or professionally to “moonlight” – so founding a company meant leaving my role.

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

After coming to the conclusion that my wife and I would be able to support our family, the biggest challenge for me was moving on from the team I had established and cared deeply about. I came to the realization that I was mentally and emotionally committed to founding my own company, and it would be challenging to truly act in the best & long term interest of the team I had – so my departure actually made sense for both sides.

4. 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 only have two managers throughout my 3.5 years at Convoy – both of whom I respected greatly. There were a lot of questions/thoughts running through my mind – was I making the right decision, had I truly considered what I was walking away from? I remained committed to the plan, and while the news was a surprise, it was also met with a great deal of support since they had taken on similar risks in their career.

5. What are you doing now?

Candidate was formally founded in January, and I’ve been full steam ahead doing everything – building the team, product, and service. After successfully raising a pre-seed, I was able to hire a team that I am thrilled to be working with every day. Even when times have been challenging (especially in 2020), having an incredible group of people who I get to partner with has made me truly excited to start work every day.

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

I had to learn the hard way that getting told “no” often is part of this job. Whether it’s come from potential investors, prospective customers, or others, it was different to receive than rejection I had faced in the past. These “nos” were either about me as a founder or my company, and at first it felt more personal. I was able to overcome this through 1) learning through each experience, 2) leaning on other founders who I developed relationships with throughout the journey and 3) using it as motivation to achieve success. I couldn’t be happier with my decision to found a company.

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

While it may be hard to swallow the risk that comes with leaving a safe role to start your own venture, nothing will match the daily joy you can find as an entrepreneur (in my experience). These two elements – risk and unmatched satisfaction – almost always come hand in hand, though.

Once you’ve started, focus deeply on your customers, users, and their experience. While the stories of rocketship growth are what we all dream of – and where the headlines are – it almost never happens without having a group of customers who absolutely love your service/experience/product.

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1. What were you doing before you quit your job?

I was a Senior VP at Bank of America, leading various information security risk related projects. It was a fantastic experience to work through multiple acquisitions of large financial institutions and related challenges.

2. When did you realize you wanted to quit your job?

As an immigrant family in the US, I’ve watched my parents start numerous blue-collar small businesses. Unfortunately, the businesses never resulted in financial stability, which resulted in my risk-averse mentality. As time went on and my career progressed in the traditional path, the stronger my entrepreneurial itch became. Giving up a great career may have appeared to be reckless to some family and friends, but my desire to build something of my own was too great to ignore.

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

My family (wife, 2 year-old daughter, a newborn son) and a mortgage were at the forefront of my mind. Being risk-averse, it took many years to make the jump while reading the popular startup books/blogs and searching for the right timing and opportunity. Eventually, I realized that there was never going to be the right time to make the jump. I overcame the fears by writing down the “worst-case scenario” on paper. When I saw that the “worst-case” was getting another white-collar job in a year, I couldn’t risk not taking a leap at least once in my life. I imagined what stories I wanted to tell my kids when they become older. My wife’s wise counsel and sounding board to balance opportunities and risks were valuable. It’s essential to prepare and bring your family along for the entrepreneurship journey (aka “no paycheck for a while”).

4. 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?

To be honest, that day is a blur. I was really nervous, but after I put in my notice, I never looked back. I just made sure to leave on good terms just in case I needed to go back and ask for my job back. Here is the journey entry from that week:

I quit my job this week. Glad to be trying something different.  Friday is the last day.

Tomorrow is Thanksgiving.

[My son] is starting daycare full time next week.

Mother in law is leaving this Saturday.

Weblife [product] demo is on Monday.

I will have no paycheck starting next week.

I.AM.AN.ENTREPRENEUR.

5. What are you doing now?

I work for the company (Proofpoint) that acquired the startup that I co-founded (Weblife) with two other co-founders. We had a successful exit after three years.

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

I knew going into it that I was starting from zero, and needed to have a beginner’s mindset. I expected 100% on the job training. Throughout the startup journey, there were challenging times where everything was pressure tested (e.g., running out of money, stagnant growth). I was lucky to have a team of co-founders that trusted and relied on each other. Eventually, we made it through alive! I am thrilled with the decision to make the startup journey.

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

Make sure to have the foundations covered before making the jump (I recommend in the following prioritized order):

• family support
• co-founders you trust
• problem you want to solve

Also, have a beginner’s mindset and learn as much as you can during the journey. The experience we gain and the network we grow during the journey will be more valuable than the startup’s outcome. We can always do another startup! 🙂

 1. What were you doing before you quit your job?

I worked as a Software Development Engineer II on the Amazon FireTV team. I joined Amazon after graduating from college and worked there for 4 years. I worked on the Alexa Media Player that plays music on most Alexa-enabled devices, including FireTV.

In parallel with working at Amazon, I spent my 4th year pursuing a Computer Science master’s degree at Cornell University. It was a busy year!

2. When did you realize you wanted to quit your job?

I’ll prefix this with the fact that I always wanted to start a company one day. I knew that it wasn’t a question of “if” but “when”. While working at Amazon, I wanted to learn everything I could so that one day I could start a business. I decided to try as many “Amazon experiences” as I could handle. I owned several projects within FireTV and Alexa over the years, helped to release several devices and later I even helped to facilitate a PR demo of a new FireTV device. During my second year, I won an Amazon ideas competition, and had an opportunity to present the proposed product to over 40 different audiences. Now, I consider this “pitch practice”, but back then I didn’t know I was “pitching” a product – I was mostly interested in their feedback. After all of these experiences, I felt well-equipped to start my own business.

The time for starting Spiral aligned very well for both me and my co-founder, Andrew DiLosa. I had just finished a few projects at Amazon and graduated from Cornell. The summer after my graduation was the perfect time to start a company, and that’s exactly what Andrew and I did.

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

I’ve dreamed of starting a company for so long that in order to stop me the hesitations would need to be quite substantial. My parents were very supportive – they knew I wanted to found a startup for a long time. They also knew I would regret not doing it more than the possibility of losing some money or not enjoying the startup rollercoaster journey.

One hesitation I had was the financial aspect of founding a company from scratch. I knew I would have to live without a paycheck for a few months or years. During my time at Amazon, I purposefully saved money that I could spend on my future company. Once I had gathered enough finances to cover a few years of living expenses, I knew it was time to go for it.

Another hesitation I had was around leaving my Amazon team (Alexa on FireTV) – I loved working there. I kept learning something new everyday and I was enjoying my time on FireTV. In the end, I realized that I would forever regret missing this opportunity if I did not take it, and that it was the right time for me to start something new.

4. 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?

My manager and I have gotten to know each other very well over the years and become very good friends. My manager supported my Amazon endeavors over the years like nobody else. He listened to my ideas, helped me to propose them, and supported me throughout multiple journeys as I tried to implement various projects within the company.

On the day I put in my notice, I flew into Seattle after my last day at Cornell and went into a 1:1 with my manager. He proposed a new growth opportunity to me, as he often did, and I told him that I really wanted to start a company and that now seemed like the right time for it. I think he completely understood why I wanted to become a founder based on the number of projects and ideas I proposed while at Amazon. He looked both happy and sad, and that’s exactly what he said – he was trying to keep me on the team, but at the same time, he was also very happy for me for starting a company, which I’d dreamed of for a long time. He knew me very well, so he understood that there was no way to keep me once I’d decided to change paths. I’m still very good friends with my manager, and I really hope we get to work together again one day!

5. What are you doing now?

I’m the co-founder and CEO of Spiral, a Seattle-based AI company that scans customer feedback and detects emerging issues before they escalate. I meet with customers, fundraise, lead product development, do business development, conduct hiring, and anything else we might need at Spiral.

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

I wish I knew more about customer discovery. As typical engineers, we started our startup journey with building a cool app. We created an AR app for teleporting others into the same room. Eventually, we learned that a cool app doesn’t necessarily make for a good business. We pivoted completely and worked backwards from the customer to define our new product. Here is how we learned customer discovery:

While working at Amazon, we were getting a lot of customer feedback in various forms and couldn’t always tell which bugs were more important than others. We became curious if other companies also collect customer feedback and apply it. After conducting over 70 customer interviews, we found that most companies collect tons of customer support conversations, but it’s often hard for them to find key customer issues. As a result, we started to take in companies’ customer support data like emails and chats, and detect emerging problems before they blow up.

And yes, I’m very happy with my decision – I’m glad I took the leap and founded Spiral! These were the two craziest, quickest, and the most challenging years of my life! Even if my startup journey would have ended for me today, I would say that the learning experience alone was totally worth it. I’m not sure I can think of any other way to gain this experience.

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

Here are a few pieces of advice that would have been helpful to know from the start:

Just go for it. When contemplating founding a company while working elsewhere, don’t worry about the current state of the idea and the product you have developed so far. It takes months or years to get to the right idea. Most founders I know iterated or pivoted a few times in the process so it almost doesn’t matter what you start with. It takes time to find the right problem and solution to base your company on and, in fact, that’s the goal of the first two years of your journey. All of this is hard enough to do without a full-time job and even harder when you have one, so my advice is if you’ve been wanting to start a company for a long time, have a plan in mind and enough resources available – just go for it.

Don’t be afraid to pivot. It’s very rare for a startup to be successful with the initial problem and solution they started with. Most founder stories I have heard always include a twist and a pivot in one way or another. If you’ve exhausted all the options for tackling your current problem and your customer discovery is in the “meh” state, think about other problems that came to mind over the past few months. A pivot symbolizes an ability to iterate, responding to a market change, or taking a new customer behavior into account, so it’s no surprise that many successful businesses have pivoted in the past.

Don’t write code (it’s a challenge!) before you hit at least 50 customer interviews. Customer discovery is everything. The most common mistake I see is implementing a product without any input from your future customers. We’ve made this mistake at Spiral – luckily, we learned customer discovery at Techstars, so we were able to get back on the right track pretty quickly. Also, customer discovery never ends – it’s a continuous loop of asking customers about their problems and verifying if your current solution is solving the same problem.

1. What were you doing before you quit your job?

I spent two amazing years as the Director for Product/Design at TINYpulse, a Seattle-based employee engagement company. Prior to that I spent 10 years at Microsoft after graduating from the University of Washington in 2006.

Throughout my career journey I always felt like an entrepreneur/intrapreneur at heart and venturing out to make an impact in my own way was always a career goal of mine.

2. When did you realize you wanted to quit your job?

I guess you can say I gave TINYpulse 2.5 years notice versus 2 weeks :). Working at TINYpulse was a dream come true for me, and a huge part of that had to do with the support leadership gave me and the team. I remember interviewing with David Niu, TINYpulse’s CEO and he was really keen in the interview to learn about my goals and ambitions. I told him in the interview after making a big impact over the next several years at TINYpulse my dream is to start my own thing, and he supported me every step of the way. I always felt the best way to land and prepare for your next role/venture/adventure is to do a damn good job of your current one, and that’s what I attempted to do before leaving.

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

The biggest question in my mind was around how I could pursue my passion and still support my family, as my wife wasn’t working and was home with our two young kids (a much harder job than I had, I might add!). This was also part of my “why” behind wanting to start my own business. I wanted to create something my kids would be proud of and make an impact as a founder. Tactically speaking, figuring out things like insurance benefits and making sure I’d have enough of a base salary to live off of were huge. I know I wanted to make the jump so really the logistics were the only barrier (that said barriers like that can often pile up and prevent people from making the jump). Our startup’s runway wasn’t just about the startup’s survival, but my entire family had a “runway” in many ways which was attached to the company’s success and that could be overwhelming to think about. My co-founder Andrew was in a similar boat and that really helped! I overcame much of this through networking with others who had followed this same path – and I soon learned many perceived barriers were not as daunting as I assumed.

4. 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?

It was tough. I loved the team at TINYpulse. I also wanted to do things the right way, and was able to work out an arrangement with our leadership team that let me ensure the transition happened in a gradual and effective way.

The day I communicated my decision was tough – I wanted our CEO and my manager to be the first to know and telling them was not easy. We had lots of exciting things happening at the company (as with most scenarios like this there is never a perfect time to leave) and I didn’t want my manager and team to be disappointed and feel I was abandoning them in any way.

People leave jobs for many reasons, and while not always possible I find it best to run toward things, not run away from things. I was making this decision because I was running towards a new opportunity. Thinking that way made the conversations easier and I was surprised at how supportive everyone was.

5. What are you doing now?

Living the dream! It’s been an amazing year+ growing our business, Humanly.io, and bringing equity and efficiency to high volume hiring processes. It’s been a blast growing the team, adding new customers and delivering on our mission in automating candidate screening, scheduling and engagement at scale. One of the biggest parts of our success has been centered around bringing others along on the journey with us so it’s been great to have folks at TINYpulse, Microsoft and other companies we’ve worked with cheer us on!

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

The importance of surrounding yourself with audaciously ambitious voices. You need to be practical as a founder, but not TOO practical. Having people around you that do more than give advice but push you through their irrational audacity is big. You can never think big enough, and sometimes it’s too easy to think your “big” thinking is big enough.

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

My main advice I’d give, and one I live with when making any life decision is to never start the decision making process by asking yourself “would I regret doing this?”, but instead start by asking “would I regret not doing this”. When you think in those terms often you could make the argument that you are risking your life (happiness, future…) by staying put in your current situation.