New Adventure 2021

Apologies: This is a super long post, but because of the details, I had to hold back for a few weeks.

I have decided to move on from Treasure Data and join a small startup named Warmly. It’s an exciting change but I certainly have feelings of sadness for leaving people I have grown to love and anxiety about starting a new position that will stretch me outside of my comfort zone.

In 2018, my year of mostly rejection, I was passed over by dozens of companies. It really freaked me out. This time, I had hardly started looking and was presented with 3 very good offers. All were from startups ranging from 10 to 55 people. It just goes to show that luck and timing are a major factor in finding work.

How to decide?

The three companies all had things going for them. They all seemed to have a good chance of success. I liked all the people. They were all startups. I needed a way to make this decision which would have a major impact on the next few years of my life at the minimum.


  1. Company A – 10 person startup. Exceptional people. Broad needs.
  2. Company B – 55 person startup. Easy B2B thing to design.
  3. Company C – 55 person startup. AI thing, seasoned engineers. More responsibility.

What did I want?

First, I wanted to have more of an impact. At Treasure Data, I had become somewhat bored. I didn’t have an interesting challenge to tackle. I thrive on being impactful and valuable. Each company scored decently on this front.

Secondly, I wanted to feel inspired by the work and the people I work with. This is harder to measure. You only get a little bit of time to evaluate people.

Interviewing and Researching

The recruiting process was pretty good for all three. One company was VERY aggressive with their tactics. The CEO offered multiple times to come to my house for a Covid (socially distant) walk to talk about it. For two of the companies I spent significant time with them doing free consulting, A.K.A mentoring.

I am happy to mentor companies and do it all of the time anyway. In my mind, I wasn’t interviewing, I was helping. However, it also had the added benefit of letting me see what it would be like working with them full time.

Two of the three companies also had me meet their VC Investors. This was eye-opening and very helpful. It made me re-evaluate how I have been avoiding founding a company myself.

I still needed a framework to make the decision. I felt like every time I spoke with one of them, I wanted to say yes right there.

Future Regret Minimization Strategy (FRMS)

I developed the FRMS based on my history. There are multiple decisions in my past that I deeply regret. I could have joined some really successful companies very early and made a fortune. I could have stayed at Marketo one extra year and made a significant amount of money. I regret these decisions.

I didn’t want to regret this current decision even though it would be very possible to end up that way.

The first step in this framework is to imagine you chose each company one at a time. Then you you imagine the companies you did NOT choose and vary their outcomes. I used a 1-10 metric for regret.

  • 1 = No regret, happy
  • 5 = moderate regret, neutral
  • 10 = highest regret, miserable

With the framework, I made the following judgements:

Choose Company A

Company A OutcomeRegret for BRegret for C
A Does Terrible77
A Does Medium55
A Does Great11

Choose Company B

Company B OutcomeRegret for ARegret for C
B Does Terrible108
B Does Medium97
B Does Great84

Choose Company C

Copany C OutcomeRegret for ARegret for B
C Does Terrible108
C Does Medium87
C Does Great61

If you look closely at the regret levels, company A has the highest levels of regret if they did well. Of course, if they did poorly and others did great, I would feel some regret, but not as much in reverse.

So based on this it was clear that company A (Warmly) was the winner for me. I had the most amount of future perceived regret if they did well and the least regret if I chose to go with them.

Role and Responsibility

My title will officially be Head of Product Design and Executive Coach. Unofficially, I always loved my Mayor, Awesome Town title. The founding team is fairly young, and they asked me to do some executive coaching. This kind of mentoring has always been a hobby of mine and I am happy to get a chance to step it up. I remember Lisa Sanders-Nakahara from my first months at Treasure Data doing that role. She is an inspiration for me in that regard. I hope I can live up to her example. I always felt some of Treasure Data’s problems could have been avoided if they had kept Lisa onboard.

One person I am especially excited to work with is Carina Boo. I hired Carina as an intern and then a full time designer while I was at Marketo. I asked her to take a gap year of school to work for me full time. She has always been so motivated, smart, creative, and productive. She eventually landed an engineering position after school at Google before co-founding Warmly. Together, we are going to tackle product and design challenges. I can’t think of a better person to work with.

Work Environment

I am fully vaccinated now and am thrilled to be able to go outdoors. My hermit days are at an end! However, I am unsure about whether an office is better than a distributed workforce. My Treasure Data team has been very productive, although I do miss the little serendipitous moments you get when you share space. I miss having lunches with people!

As an experiment, I am going to have a few Warmly people over to my house to work. I have some extra space and very good internet access (Fiber!!). My pet tortoise Ningame and dog Leroy are friendly and the food in the area is solid. I don’t know if this is a great idea or not, but I kinda stoked to try it out.

It’s actually turning into a great excuse to fix up some stuff around the house, like replacing carpets and flooring. Worst case scenario, we stop doing it, but I have high hopes. A true silicon valley startup!

OK, Wrap it up!

Im going to miss the best design team I have ever put worked with. They have been great and I will measure all future teams agains their example. My eyes, however, look the future. I am learning the details of b2c network effect products and how design differs. I am excited to change my work patterns.

I don’t have any headcount yet, but when I do I will be sure to let you know. In the meantime, keep the dream alive!



8 responses to “New Adventure 2021”

  1. Robb Beal Avatar
    Robb Beal

    I see what you did there at the end.

    Glad to know you avoided the rejection.

  2. Courtney Avatar

    Yay Glen! I’m so happy for you and that you choose Company A. And ever MORE excited that you and Carina are reconnecting. Kismet!

    1. Glen Lipka Avatar
      Glen Lipka

      the moons hath aligned!

  3. Abdul Avatar

    Thanks for sharing your regret framework FRMS. All the best!

  4. Rama Avatar

    Great Glen! All the best for the new endeavor. Though I am a bit sad and will miss your heckling but I am excited to know about your new opportunity. All the very best!!

    Let me know if we can catch up for lunch sometime.

  5. Daniel Lipka Avatar
    Daniel Lipka

    But you didn’t mention what Warmly does. Anyway, it looks interesting and anything that makes zoom less terrible would be wonderful. Last night, I had a zoom meeting for a Board that I’m on; I’m still relatively new to the group and it would have been great to get some background information on some people so I can put their comments in context (there were 12 people on the call). And if they can add a feature that makes it look like my eyes are always facing towards the center of the screen/camera, that would be sweet.

    Congratulations and good luck.

  6. Chris Avatar

    Nothing worse than being bored. Glad you found something that you’re excited about!

    And I wish I had your confidence while interviewing. It feels like a lot of interview processes filter out introverts.

    1. Glen Lipka Avatar
      Glen Lipka

      Remember that the goal is just as much for you to learn about them as them learning about you. I’m introverted in general too. In an interview you have to try and be yourself. The right people will like you. The wrong people won’t.

Whatya think?

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