Before you begin

Reflections on a startup journey (Chapter 1)

I founded AppSheet in Seattle in early-2012. The company was acquired by Google at the start of 2020 just before the pandemic took over our lives. Now that it has been a decade since the journey started, I’m writing a series of articles to reflect on some things before I forget them entirely. My perspective might benefit others who pursue the tech startup path as founders or as team members. But I season that statement with a big dollop of skepticism. Every startup journey is different, and my perspective is probably over-fitted to my unique situation. My takeaways from these events could well be completely irrelevant to another situation and also maybe dated. So please read with skepticism and at best, treat these articles as opinions not advice.

There are four questions to ask yourself as a startup founder:

1. The reason: Why am I doing this?
2. The risk: Is it sensible for me to do this?
3. The people: Who am I doing this with?
4. The plan: What are we going to do?

Depending on who you are and your past experiences, the order of these questions and their importance varies. However, all four are crucial questions to ponder.

In my case, I had turned 40, I had been at Microsoft for 12 years and I was disillusioned and unmotivated by life in a big company. I had managed teams of different sizes and enjoyed driving V1 innovation. I had been promoted aggressively and was compensated very well, but I was tired of being mediocre at company politics and having my passion projects killed. I missed building products myself (my time in code had dropped to less than 5%). I was also self-confident bordering on arrogant, didn’t know what I didn’t know, didn’t have much experience outside of Microsoft technologies, and hadn’t cultivated any relationships in the startup community in Seattle or the Bay Area.

My answers when I started

1. The reason: I’m doing this because I’ll be happy doing it without the stodgy big company overhead
2. The risk: If I don’t do it now and stay another N years at Microsoft or another big company, then I’ll run out of time to take the risk.
3. The people: <I didn’t really think about who I’d do it with — did I say I was arrogant?>
4. The plan: I am going to do something that has global impact < vaguely, I had the notion that we’d allow consumers to “program the internet”>

In hindsight, the only question I really addressed properly was #2. It is a very important question because you are never doing a startup alone. You are always doing it with your family and they carry the risks with you. In my case, my wife had quit her software job, changed careers and had just been admitted to medical school (so no salary for the foreseeable future but some outlay for college fees). I had two kids, ages 14 and 12 at the time, both going to public school, but both probably headed to private colleges. However, we don’t have an expensive lifestyle and Microsoft had compensated me very well over the previous decade. I decided that I would do the startup only if it didn’t cause us to change our lifestyle. We’d go for the same vacations, and buy the same clothes, eat out as often as we would otherwise do, etc. At least, that’s what I said, I did the math and the numbers said it was fine. I think in reality, you’ll find that when you go years without a salary, you do get more cautious about spending money and even if you don’t, your family might. So it is something you need to take a real hard look at before getting started.

This is especially important if, like myself and other fortunate software engineering types, you are already in a well-paid job in a big tech company where the job is cushy, work-life balance is the first priority of corporate HR, and you can complain about first-world problems like the number of kombucha flavors in the free micro-kitchens and how your manager isn’t giving you enough extra headcount. So make sure to understand that if you are just frustrated at work, you and your family can probably take a year off, travel the world, and then return to a job at a big company, perhaps even the same company. And financially, it would be a lot less risky than choosing to found a startup. It’s different if you are very early in your career (relatively little to lose, no family commitments, etc). But once you are a decade into your career, with the house, the mortgage, the 401K, the family and kids and the Hawaii vacations, it becomes a lot more risky. <Yes, this is insanely privileged. We live in an upside-down world where the ability to write some mediocre Javascript is “worth” much more than the ability to teach children or care for the sick. Yet that is the reality of software engineering careers today, and once you are aboard the corporate gravy train of SaaS/data/ads/ML/blockchain/cloud/5G/no-code/crypto, you have to think carefully about whether and when to hop off.>.

Do a startup because you want to enrich your life in a non-financial dimension. Simply never do a startup to make money because it is a low probability outcome. When you are doing a startup, there are enough stresses without also worrying about the financial stability of your family.

For my part, I took most of our money out of the stock market and put it into conservative investments. This was at the start of 2012, and by doing so, I missed the stock market boom. But that was and is ok with me. I have always been conservative with personal finances and I simply could not afford the risk of losing a significant chunk of our savings at a time when I wasn’t going to receive a salary for the foreseeable future.

My answers in hindsight

Let me try to answer those four questions now. With the benefit of hindsight, here’s how I wish I had thought about them:

1. The reason: Why am I doing this? “I feel I can do more. And I need a change, I need to learn.”
2. The risk: Is this the right time for me to do this? “This is a risky time for my family. Maybe I should stay at Microsoft for a couple more years, sock away some money, and learn more about startups in the meantime. Or maybe I should join an established startup for a couple of years and learn what it’s like.”
3. The team: Who am I doing this with? “I absolutely need great co-founders with deep mutual respect and trust. I cannot do this alone.”
4. The plan: What are we going to do? “This is a pretty darn important thing to figure out before quitting my cushy job at Microsoft!”

Preparing for the journey

So indeed, I was wildly unprepared for the startup journey in important ways :

(a) I had no experience with startup culture,

(b) I was a tech guy/engineer with no business experience,

(c) I did not have a co-founder or a team,

(d) I was fuzzy about what the company was going to do.

But all that said, I was well prepared for the startup journey in important ways too, and not all startup founders have these advantages.

(a) I had self-confidence. I was sure if things didn’t work out, I could get a job back at Microsoft or another big company (btw, only partially true). More importantly, I had misplaced self-confidence that by sheer will and effort, the startup would succeed. As it turns out, self-confidence is over-rated, but what is valuable is a sense of self-worth that isn’t based on short-term success or failure.

(b) I had good connections to people at Microsoft and before that from my academic career,

(c) I had money in the bank and therefore financial stability,

(d) I was a good hands-on software engineer, a good communicator, and I loved to work very hard at whatever was needed,

(e) I had started, hired, and led small and large teams before.

My learnings from this period

Though I didn’t know much, I was sensible enough to try to learn. I talked with many people in the Seattle startup community. My friends in the bay area introduced me to people they knew and those people created time to meet with me. This was strange and different from my past experiences at Microsoft. People were generous with their time and encouraging in their support. This is so unlike a big company where most meetings are transactional and most people were territorial. As an aside, they tell me Microsoft culture has changed some now with Satya at the helm.

I have three big learnings from this period:

1. People give you a lot of well-meaning advice but it is often contradictory — — so the really important thing is to figure out who/what to listen to and who/what to politely ignore. This is not at all easy. People who are experts at something (let’s say a VP from Microsoft) may be completely wrong about what works at a startup. At this stage, I talked to a lot of money people (investors of various kinds). That was a complete waste of time and in fact actively detrimental(see the next point). At this stage, you only want to talk to people who have been enterpreneurs and the only thing you need is encouragement (and also practical things like — — how did you incorporate, do you know a good lawyer who doesn’t cost a fortune, etc).
2. You have to be at the right stage and bring the right content into the meeting in order to get the most value out of it. Unfortunately, people only volunteer their time once, so if you don’t make the right impression on them, then that is a lost contact. I made the mistake of meeting too many VCs early — — the conventional wisdom is to meet VCs early and often, build relationships, seek advice, etc. I believe that to be completely wrong. Every VC I met was somewhat curious about me but really wanted to know what I was working on. When I said “I don’t know yet, I’m figuring it out”, you could see them promptly lose interest. And if I said something vague like “I’m trying to enable end-users to program the internet”, they’d ask the next level question which I didn’t have answers for and then they’d write me off as someone who didn’t know what he was talking about (true!). They are busy people and I shouldn’t have wasted their time. Made it much tougher to get them to meet me and take me seriously later when I did have something concrete. Besides, you don’t want money from VCs initially anyway (more on that in a subsequent article).
3. Someone told me it would take a while to “detox” from Microsoft and that was really so true. I didn’t understand it at the time, but I sure do now. When you are at a big company, you live in a cult and you conform to the cult brainwashing via regular infusion of a cocktail of toxic drugs — performance reviews, bonuses, stock grants, manager pat-on-the-back, large teams to manage, promotions. This stuff is pumped daily via an IV-line straight into your bloodstream. You think of people in terms of their ladder levels and you judge yourself based on some review grade handed down by your manager. The system evaluates you based on conformance and you try hard to conform. You never evaluate yourself based on actual value generated in the world, or actual people you have helped, or actual customers whose problems you have solved, or actual daily satisfaction you feel. Until you finally leave. Then, after you go through the withdrawal symptoms, you eventually stop thinking of yourself in terms of your ladder level and your review and whether you will or won’t get promoted. And you stop thinking of your work in terms of what your VP said. Even your sense of self worth needs to be entirely reframed outside the levels and titles and review ratings you have grown used to. Some people never detox — they just try to build that same culture in their startup, but it never works. If you are lucky, you eventually detox and you start realizing it’s just you and your laptop. Gloriously, even though you suck at whatever it is you are trying to do at the start, you have a shot at fixing it and nobody else can kill your project. Only you can!

Indeed, perhaps that is the best way to end this first article. You know you are at the beginning of your journey when it is you, your laptop, (and hopefully a couple of others with their laptops with you) and by default you suck at whatever it is you are trying to do. From there, everything can only get better. And it sure does.

In Article 2… laying the foundations for success (or rather, if you fail to do some of these things, your startup house _will_ probably come crashing down).

“… I have only come here seeking knowledge
Things they would not teach me of in college
I can see the destiny you sold turned into a shining band of gold …”

— — The Police. Wrapped Around your Finger