Kenny Lee, Co-Founder of Weblife

September 15, 2020

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.


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{7da1b4016315e6906389b7680f0f0ab0dbfee16dff356723890b92cef8bfc446} 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! 🙂

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