Doing the High-Wire Act

Just don’t look down

DALL-E Generated

I’m having an allergic reaction to all the glossy playbooks and dry market outlooks.

Startups are freakishly hard. We haven’t talked about that enough during the hype market. We’re STILL not talking about it.

The reality of building something from nothing is that it often involves a string of near-death experiences and high-stakes moments. It’s not all up and to the right. There are moments that really matter, punctuated by anxiety, long odds and leadership juggling acts, when the fate of the company hangs in the balance.

Hard to describe but if you’re a startup founder or operator, you know the feeling — or you soon will. It’s like walking a tightrope with no safety net. A high-wire act.

In 2023 we will see more startups face these moments. That’s normal. It’s why startups are not for the faint of heart. But I feel compelled to acknowledge the struggle because we don’t observe it in public, these are quiet battles. Founders don’t want to show how dire or stressful it is (rightfully so). Operators are too heads down to air it out. It’s under the surface.

Whether you face your high-wire act in 2023 or in the future, I’d like to offer some advice. I hope it helps a little.

Note, this isn’t VC advice. It’s what I’ve learned from 5 startups and facing many of these moments as an operator. Here we go.

When stakes are high and options are few:

The do-or-die startup moments typically fall into one of 2 situations.

Most come down to getting a deal done. This could be a key customer contract, an M&A transaction or a fundraise. It could be a competitive government RFP or signing a critical commercial partner. One way or another, the high wire act requires getting a deal done, typically on a short fuse.

The other situation, which is common at early stage, is high-wire execution on a key product and resulting traction, knowing there’s no engineering time do-overs. You gotta SHIP.

There’s plenty of other anxiety inducing moments in startups but I find that the intense nail-biters are usually one of these two scenarios. Close a deal. Or ship a product. Under impossible constraints and while trying to keep a team focused and motivated.

It’s called a high-wire act for a reason.

just don’t look down

10 things to remember during a high-wire act:

1. Lead fearlessly, with trust-building in mind. This is the time to provide clarity to your team and explain what is at stake. Showcase how you are creating options, making decisions and playing for the benefit of the team. The worst thing you can do is pretend that it’s all rosy when the team can read your anxiety. Startup teams are resilient but they expect to be in the loop, it’s a start up after all. Make sure your team has enough business and situational context, they don’t need to agree but they do need to understand. No one wants to follow a leader that hides the ball.
2. Transparency is laudable but not always possible. You might be working on an M&A transaction or strategic partnership that requires confidentiality, it’s the nature of a deal process. There are moments when you cannot be fully transparent and you don’t want that to be seen by the team as a betrayal or obfuscation. Try to thread the needle. Give the context you can, outline the constraints and “what if’s”. Invite questions but don’t play favorites with information and people based on personal affiliations. Protect the process.
3. Build an inner circle you can trust. There are times when the people you need to get it done aren’t necessarily the OGs or the most senior people in the room. When the stakes are high, you’ll need a fellowship-of-the-ring moment to rally the right team. Pick individuals you can trust. Truth seekers who will serve as an objective sounding board. Grounded leaders that will respect confidentiality and put the company first. Principled leaders that will see things through to the highest standards.
4. Deals take time. Whether it’s a partnership, M&A exit or long sales cycle, it takes about 6–12 mo to get a meaningful transaction done. It’s a rare and very fortunate situation when both parties are so motivated that it gets done in a few weeks or months. Be realistic about the timeline and manage it closely with respect to the runway.
5. Time kills all deals. The opposite is also true. Deals sag when things take too long, so won’t be too patient. Market conditions can shift. Companies can change priorities. Champions could lose their nerve. Pacing and momentum is critical. To get a deal done, keep up the urgency level, create forcing functions along the way and strengthen interpersonal commitment. Whatever you do, don’t let legal hijack the process and derail it. Keep it moving because any deal that isn’t clearly progressing is default dead.
6. The last 20% of any deal is the hardest. You’ve talked terms and ready to paper it, this seems like the home stretch but this is where deals take on an endurance sport like quality. The slog of final negotiations, reviews up & down the chain and the vibe of the legal interactions can all make the last 20% of the process quite complex and exhausting. Expect and anticipate the 11th hour surprises and persevere. Work harder and smarter than the other side to figure out how it gets done.
7. Crank up the intensity and energy. Don’t be afraid to push your teams to the limit. It’s counterintuitive but if you’ve hired well, you have people who would rather give it their all than face defeat. And they’ll resent you if you deprive them of the opportunity to do that. Simply ask your team to step up (in concrete, actionable ways) and you’ll be shocked at what they can do. Quite likely that you’ll unlock a new level of execution you didn’t even know was possible. The thrill of doing hard things and taking full ownership brings out the best.
8. Emotionally self-regulate, it’s your job. When you are under crushing pressure, you can’t let the cracks show too much. Teams rarely do their best work when they are dealing with the emotional outbursts of their leaders. It’s a distraction. Find a way to self-regulate by setting an intention for how you want to show up and using healthy habits to reset (e.g. walk around the block, help someone else). Self-coaching is key.
9. Leave it all on the dance floor. Don’t let pride or clinging to status get in the way of going that extra inch that could make the difference. Set the ego aside and just get the result. Ask your teams to do the same. You’ll never regret trying your best to walk that tightrope and your people will respect the heck out of you for it.
10. Never sacrifice your integrity. Don’t lie. Don’t cheat. Don’t put anyone else into an embarrassing situation. Great leaders find a way without.

One more thing for Founders, there might come a time when your incentives diverge from investors or the team. Own that. Do your best to give everyone a win. It’s all part of the game.

You can find me on Twitter @annbordetsky or subscribe to my substack. Drop me a line to let me know any feedback or thoughts from this post.

Disclaimer: Views and opinions here are my own.