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The last month, April 2024, has been a sobering time of calling friends, reaching out, networking,
and generally trying to find some space and some security. While not all of my endeavours were successful, with the help of a friend, was able to get some groundwork laid for staying afloat. So since, I do have a bit of a break, I thought Id reflect and write down my thoughts. Just some observations, really, from the last few years.
So, to start, I don't blame anyone. I believe most people work and act to the achieve the best results for themselves and for the projects they care the most about. In fact, its how I usually try and find folks to work with. I find the people like me, care alot about technology and getting things done. Who care a lot about people and want to create a humane place to get that work done.
To that end, working with my old startup was on point. People cared, we only ever lost a team member to our culture, once, and that is out of seven years. Which, to me is a great win.
Now no startup is perfect, some things I have been thinking about on reflection were:
Now, im **not** here to air out my dirty laundry from the past seven years and im certainly not going to do it from my own one sided point of view. I just want to discuss those points on their own merits and explain how I think they helped put the startup on the back foot. _Also, I just want it out of my head_. So let's dig in.
Just do it. Nike
Think big. IMAX
Belong anywhere. Airbnb
For us,
Widgets are the bottleneck for your companies growth... We are 'the' Widget hub... We focus on getting Widgets done faster.
I realize that comparing yourself to Nike, IMAX, etc is not what you do as a startup. You find your fit. I've often heard it doesn't matter if you pivot 100 times or stick to a single plan and execute. At the end of the day your only comparing lottery tickets. Those tickets can look vastly different depending on the leadership. But I have a problem with not being able to solidify a goal after three years. I need to have something I can look to, to turn to, to understand vision when no one is around. When im trying to figure out the most important next step for engineering. I look left, look right and look in. Taking those internal mantra's and making them material.
So is it the most important, no. But it helps keep all departments rowing the same direction. Something we really needed every day, it was missing.
To that end, I think what I could have done better here, was in shepherding the consensus and driving it home with investors. If we believe that our special sauce is X, then the board should agree so they don't have any surprises. I think half the time what we spoke about internally was in stark difference towards the expectations of others. Even if it wasn't the CTO's duty, I should have made more of an effort to hold the management group to consensus. Because that's our job, brand the message.
So I think this article from Jose Gorch, did a fantastic job in outlining the issues I saw with the flat structure. Now mind you, thats just how folks work in engineering. We hold ourselves to the things we know best and trust product to do what they do best. So in essence by trusting each other, we naturally achieve great things. However, this can breakdown. It does so when the people creating the product are second and third guessed by upper management. That means, to be clear, you either hire someone as a product manager and let them deliver what your vision to the best of their ability. Or you do it, and admit you aren't clear enough to make that vision come into fruition.
It was painful for this lesson in particular. To see the inability for one team member to express, given all the process we put in place, to be successful. To time and time again hear, we didn't deliver on the promises we made. That gutted me and it gutted the team and it really rubbed me raw because the only thing in life we have is time. Wasting it is a travesty, mostly for me. But also because I/we could have focused on something better.
So is this about org structure, kinda. Its about communicating as an org, but its about leadership and what happens when that fails. I think flat orgs can work. But I don't think it works when the people involved don't understand the bottom line. If it's not clear from either top or bottom, you build the wrong thing. Thats the failure.
So I think this one was more of a lesson learned. Should have pumped the breaks on the consensus and gave people roles and expectations from day one. Namely that the upper management runs the show and that we are responsible if the company sinks. So setting expectations with the team, day one, on what happens when we miss goals and releases. We did "try" this a few times, but should have been consistent in holding people accountable to their KPI's. Like that should have been _the_ measure and we didn't keep it consistent.
One of the key things I've learned over the years is that losing money on a team is often par for the course, especially in the early stages of a VC-backed startups. In fact, it's typically a sign that the founders are investing heavily in building out their core operations and infrastructure. However, when that loss starts to become a "death sentence" for the company, that's a red flag that needs to be addressed quickly. As CTO, I found it incredibly hard to see the runway shrinking and literally doing everything I could to keep the team aligned on where I believed we could strike out for the most value.
But at the end of the day, revenue is what drives growth. So as a CTO watching burn rate and cash reserves became a think I was looking at everyday. The big thing for me, that I felt I did well was regardless of those financial challenges, I kept the focus on delivering value to our customers. Made sure that the things we were building and promising were tracked and that we communicated to the org why we were doing the things we were doing.
It really feels like a catch-22. When you have a vc backed company, you expect the vc's to bail you out. But if you can't float or show more growth in the industry, they aren't going to toss you a life raft. So the real lesson learned for me, was just slower growth. Because no amount of sweat can make other departments more effective. Given enough time, things can work out, but at a startup money is the only measure of success.
If building software is the core of your business, then revenue is the lifeblood that keeps it running. Sales are the champions who move that revenue into your company's coffers. They may be the single most important factor in keeping the lights on and things moving forward. This is a critical point - growing too fast without a solid sales strategy can be the downfall of a startup.
You can't expect sales to just magically happen. You need to know how to effectively sell your product, who the right sales folks are, and a repeatable sales process to hand off to new hires. Your sales strategy shouldn't rely on 100% enterprise or corporate deals either - it needs to be multi-faceted to stay ahead of the competition.
As the CTO, I should have been more involved in the sales process early on. Spending too much time gathering feedback from peripheral team members, while valuable, doesn't directly impact the bottom line. Being more hands-on with sales calls and even taking on a client or two myself would have given me better insight and allowed me to provide more informed guidance. Even if I wasn't driving sales, just observing and offering a technical perspective would have been hugely beneficial.
Again, this one is another no brainer. Your c-level suite, needs to be involved in all the debate. Got it? Great. Now, what do you do after spending 3+ hours in a meeting pitching devils advocate. Finding consensus, going back to the drawing board, etc etc. What you don't do is take all that strategy and throw it out the window the first chance you get.
As the face for the company. You don't hit all the points your c-suite told you not to. You don't 'read the room' and tell them them anyway.
Because people listen to you as leadership.
They hold you higher for what you say than a co-worker.
Things shouldn't surprise your co-founders or your c-suite. They should all be up on the table and discussed. Because at the end of the day, its a team effort that keeps employee's around. If your making promises that I know don't match revenue, it is a problem. Even if you 'believe' the money will materialize, its not an ethical place to steer from. Tell people, that we are doing everything but don't make promises.
So I should have quit. I should have recognized that this was a pattern and quit. I don't think you can come back from this breach of trust, I just don't. If you don't want to be made to be blamed for what someone is saying then you can't remain complicit after they have said it. It was no ones fault but my own, and of course a fear of losing my job when countless times I heard things that didn't align with what I knew to be true at the company. Whether that was to staff or to anyone. Its my own responsibility to be accountable when anyone says things that I don't agree with. So, it was a big red flag. Because at the end of the day, if a person knowingly continues to say things that are in disagreement with what you agree to say or do. Then its just them being them and you should do you.
I could write a novel on the amount of meetings that could have been an email. It's a trope at this point. But for some reason, they got so much worse near the end. Just the same meeting really.
A rehashing of the same dried leaves . Doesn't matter how many times you look. The writing is on the wall. So why are we having this meeting?
A good friend once told me that, meetings are working. They are worth looking into the camera, taking physical notes, and listening proactively. To engage in the meeting, because it's important. So
you know, I really liked that. For someone who, for years, didn't pay attention that much in meetings, I did. Which wasn't a light switch but it was good practice. To just keep my fingers off the
keyboard and try to paraphrase what the speaker is saying. Repeat it back and ask questions, even if they seem dumb, it never felt like the team made it out like I was saying something done. So if
nothing else, I really appreciated the idea, of not treating meetings like baggage but like something that is a formality of doing deep work.
You don't waste that time on pointless rehashing, you spend it with your team figuring out how to make hay into gold.
So thinking more about this, I think going forward, I will be more consistent in keeping an agenda, keeping people engaged through active participation, and really get better at treating a meeting like work. For more redundant conversations, I should have taken the time to bang the gavel, take stock of what was said, and figure out if we were just kicking the can. If we are, take those steps to re-focus the meeting and if not, embrace the new. So really, it's all about agency in those meetings, finding my own voice, and being consistent in using it to drive work forward.
So, just to reiterate, I had a lot of fun in my last adventure. Looking for new ones all the time. Feeling a bit older now and feeling like I know better how to act professionally when the world around me isn't. How my strengths in listening, and in empathizing with people are getting stronger. But also realizing, that it takes adventures like the one ive had to become a more rounded person. So the bullets I wrote out definitely weren't all my learnings, but I felt that writing those thoughts up would be better served out of me then in. So in the end, hope you enjoyed the read and if you find one of those bullets that resonates with you leave a comment. Or just bookmark.
Take from this what makes you stronger and leave behind anything doesn't serve you anymore.
Have a nice day.
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updated: 18 June 2024.