Above the water: smooth sailing. Below the water: fast paddling to stay afloat.
Building a startup is equal parts difficult and stressful: You have to confront constant challenges that you haven’t seen before, under duress, with your financial security on the line. If you’re lucky enough to grow larger, you’ll also need to master the art of staying calm while staring down scary situations that you have never seen before.
It turns out that startup challenges are actually pretty similar across companies. But since everyone generally strives to exude calm in difficult situations, it’s rare to hear about real challenges outside of 1:1 conversations. This can be anxiety-inducing – I’ve often spent weeks silently wondering “Is this normal?” about a situation that others are also quietly struggling with. Here’s a list of totally expected scenarios that I wish I had known about earlier.
Something will always be on fire
If you grow quickly, things are going to fall apart. Let’s say that your team has grown from 3 to 10 people in the last year (a common growth trajectory for a startup in scaling mode). Many of your operating models will break with this increase. Extrapolate that growth rate over an entire company over many years, and eventually your entire existence starts to feel like a protracted fire-fighting exercise.
Don’t beat yourself up too much when things are on fire.
This is normal and expected – if the wheels aren’t coming off the bus, you’re not driving it fast enough. What’s important is to make sure that you keep a cool head and adapt.
You’ll improve at telling your story
At first new products are like babies: shiny, new, and cute. But on the way to adulthood they become gawky and awkward teenagers, just trying to express themselves:
Even though your product works and your first few customers are happy, you’ll still struggle to tell your story well: to customers, candidates, or the press. To some you’ll be a small upstart with unrealistically big dreams; to others, you’ll be a derivative knock-off of some other category (“So you’re just a more expensive data warehouse?”). It’s common for some people to just get confused at to why your product exists, even if you’re successful.
But all companies get better at telling their story over time. You get to iterate on your story across hundreds of audiences; your product matures and grows into your overall vision; you build a brand. Eventually you find that your story really resonates but it truly takes time.
Don’t misread confidence as competence
For every startup topic, there’s a confidently written blog post telling you what to do and (implicitly) why you might be screwing up. This experience has never failed to stress me out – it’s a damning warning that you might not have your shit together. Whenever I’ve spoken with the purveyors of confident advice, I’ve always found it telling just how much the reality on the ground reflects the same challenges that everyone faces. All internet advice deserves a grain of salt.
The loudest or most credentialed voices don’t necessarily know what’s best for your business.
Many startup “best practices” also originate from FAANG companies with commanding consumer monopolies, and where product and engineering call almost all of the important shots. If you’re a SaaS company, especially in the enterprise with demanding customers and a robust sales motion, you likely live in a completely different world.
Luck matters a lot
Sometimes you get lucky with external forces: a relatively slow-moving market for designer tools combined with rapidly improving desktop browser capabilities allowed Figma to rapidly gain massive mindshare. Sometimes bad luck crushes you through no fault of your own: AirBnB currently faces existential challenges due to the COVID-19 pandemic.
History is written by the victors, and the degree to which luck plays a role can’t be overstated. Success requires talent, hard work, and luck, but all three are necessary but not sufficient. And if you told me I could guarantee one of the three, I’d choose to be lucky.
Some problems are unavoidable
Sometimes, you just have to do your best.
If a problem keeps rearing its head in an intractable way, it might just be an inevitability for businesses like yours. Due to the interactions of business models, technology realities, and incentives within an organization, there are some challenges that are destined to exist. Here are a few common ones I’ve seen in enterprise businesses:
- Struggling to balance new feature development vs. tech debt.
- Deciding when to break your roadmap for a large customer.
- Sales and Marketing disagreeing on event strategies.
- Enabling your sales and support teams while shipping quickly.
- Engineering getting frustrated with Design.
- Design getting frustrated with Engineering.
- Everyone getting frustrated with Product Management.
For these sorts of issues, often the best strategy is to just be as Zen as possible and do the best you can.
Whatever is going on – you’re likely not alone.
- Something will always be on fire
- You’ll improve at telling your story
- Nobody is perfect
- Luck matters