How to deal with startup transformations

Remember, this is what you signed up for.

When you start a technology company, your first few years are usually one long string of pivots. Some of these will be big pivots, and some micro. A lucky few will find that one of their pivots worked really early and they become famous. But, for most people, a startup is an act of dogged determination and resilience through adjustments until you finally find your thing that sticks.

One of the primary reasons why startups fail is that the founders simply get tired and give up. It’s exhausting to keep pivoting, sometimes it’s literally life threatening to keep going. However, you must remember that it is the very nature of the startup journey to take you to the brink of your very existence. It’s only when you look at the reflection of yourself in that dark abyss that you find what you’re made of, and what you can create and leave behind in this world.

So when you read about the “overnight successes”, just remember that most of them have a history of toiling away for years under a different name, sweeping all their pivots under the rug, and then coming into the market fresh. Voila, an overnight success…. but really it’s years in the making. It’s the story of TinySpeck becoming Slack, Talkshow becoming Clubhouse, Odeo becoming Twitter, Classtivity becoming Classpass, Saasbee becoming Zoom, and the list goes on.

Here are some tricks for bearing through relentless transformations:

1. Get off social media. Or if you can’t help yourself, then just keep an attitude of rolling your eyes at everything you read. Social media is a parade of fake highlights and VC marketing that glosses over the hard truths and realities of the startup journey. I hope for a future where social media has more truth and honesty, but as long as it’s still controlled by advertising and dopamine delivery, it’s just lethal for entrepreneurs. There is some value in keeping up on the latest memes and trends (and yes, some occasional helpful insights), but is it worth the countless hours of wasted time and false comparisons?
2. Co-founders are not equal contributors. You’re going to have a much easier time on your journey when you realize that all businesses ultimately end up with a sole founder spearheading the company. Putting aside the low survival rate of co-founder relationships, the benefit of doing it is having highly committed people who will thank you. I don’t say this sarcastically. Being a founder is a thankless job. Employees and investors rarely thank you until the very end. So it may be worth it to you to have co-founders who will thank you for your contributions and truly celebrate with you along the way. Might be just the energy you need to keep going.
3. Be prepared for constant rebirth. With every pivot, you have to take a hard look at your team. I mean a really hard look. The team which took you blood, sweat, and tears to recruit for your past iteration may not be the right team for your next. You have to be prepared to do the hardest of things. The earlier you realize that, the better, as you’ll likely run out of money and time if you don’t.
4. Delegate like a hero. The most important thing you will learn in your journey is that you don’t know shit. You have to stop hiring people to execute on your plans, and start hiring experts who design and own their own plan. When you start to take grasp of your role as an allocator of capital and upholder of culture, thats when you will be the real hero and create a cast of heroes to take the business to success.
5. Brick by brick, day by day. Transformations can be overwhelming. Break these initiatives down into micro-steps is often the most empowering way to get through it. Just don’t forget to celebrate each brick. Self-care is critical to powering through and you have to start by appreciating yourself.