Raising capital? Check out my ebook, Pitching Angels, as you prepare your pitch.
Every founder hits low points.
The product isn't finding traction. A co-founder leaves. The fundraise falls through and you're staring at the date you can no longer make payroll.
When that happens, the instinct is to give the company more of your time and enrgy. I understand that instinct because I lived it.
I've sat on every side of the table: as a general partner at the VC firm OCA Ventures, as a co-founder of VC-backed Shiftgig, as an angel investor, as a EIR and Venture Partner at 3 funds, and today as a co-founder of a bootstrapped startup. I've been through hard periods myself, and I've watched many founders go through theirs.
At Shiftgig, I believed working longer and harder would produce better results. I worked seven days a week, flew almost every week, and slept in the office during product releases. Today I fly once a quarter, take real days off with my family, and let my co-founders execute. The company is better off for it, and so am I.
Grit matters. Founders who push through doubt give their companies a chance to survive. But grit only keeps you from quitting. It doesn't tell you how to get out of a low point. As Linxin, founder of ChowBus, told me:
"Sometimes working smart is even more important than working hard. You still have to work hard, but you have to be moving in the right direction."
When the founder journey gets hard, here is what I'd focus on.
1. Protect your health and your life outside work
When founders ask me how to get through a hard moment, my first answer is always the same: take care of yourself.
Unmanaged stress turns into bad mental and emotional decisions. You get impatient. You snap at the people who need your leadership most. So start with the basics:
Sleep.
Eat, even when stress kills your appetite.
Exercise and get out in nature.
Build routines outside work, and protect them.
If your calendar is nothing but work meetings, that's a problem. Schedule family time and workout time the way you'd schedule a board meeting. Set periods when the phone and laptop go away.
Watch for the warning signs of burnout. You're too tired to think straight. You start losing optimism. You catch yourself thinking a 9-to-5 job would be easier. You're short with your team, your spouse, or the people closest to you.
These signs tend to show up when payroll is at risk, when you lose teammates or co-founders, or around years four to six, when the journey starts to feel long.
This isn't about perfect work-life balance. But being all in on your company doesn't make your partner, your children, or your health needs disappear. Your family and friends will be there before, during, and after the startup. The startup won't last forever.
The worse things get at work, the more these routines matter. They aren't a reward for fixing the company. They're how you stay capable of fixing it.
2. Have someone you can tell the truth to
Your co-founder and executives are essential, but in a crisis they're usually as close to the problem as you are. And you can't share everything with your executive team or your investors.
Every founder needs at least one person outside the company they can be fully transparent with: an experienced founder, mentor, advisor, lawyer, or accountant. Ideally, someone who isn't day to day. A peer group of founders at a similar stage can serve the same purpose.
Good support starts with listening. They may help you walk through your options but they don't make the decision for you.
When COVID hit, some of my portfolio companies saw their revenue drop to near zero. The founders didn't need me to tell them what to do. They needed someone to listen, then help them think through cash, runway, staffing, and scenarios. The decisions were theirs, and they made them but a good brainstorm can be helpful.
Build these relationships before you need them. If the first time you call an advisor is when you're nearly out of options, the rapport and trust has not been built up.
3. Give yourself time to make a clear-eyed decision
Rest and perspective don't replace confronting the numbers. They make it possible to confront them well.
Start with financial triage. What must you spend? What can you cut? How much runway do you actually have? The right balance on cash and burn, not on how frightening the moment felt.
Runway gives you time to think and pivot
Ryan Coon kept Avail's finances conservative and its unit economics strong, which preserved his control and his options.
Pat Vihtelic built Home Chef to profitability with real cash in the bank, so he never had to take a deal with Kroger out of necessity.
Once you've bought time, ask honestly what isn't working. Is it the product, the customer, the team, the co-founder relationship, or the fundraising story? Be willing to admit a mistake and change direction. At Shiftgig, we expanded too quickly after raising, before our people, processes, and product had caught up.
Your future is bigger than this company
None of this guarantees your startup survives.
If your company shuts down, you still have a job to do. Tie up loose ends and communicate clearly with your team, customers, and investors.
But then take time to decompress before rushing into the next thing.
Leaving is hard even when it goes well. Pat told us this about leaving Home Chef after a successful exit:
"I missed the camaraderie and the team aspect of it... It was tough to leave for sure. Bittersweet, no doubt. I still miss it sometimes."
Failure doesn’t automatically become wisdom. You need time to reflect. Investors don't back 2nd time founders because they failed. They back 2nd time founders who can explain what went wrong and what they'd do differently.
Protect a routine outside work. Build a trusted relationship before you need it. Know your runway before the next hard period arrives.
What have you stopped doing for yourself because you're waiting for things at work to get better?
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Planning your next raise? Check out my ebook, Pitching Angels, as you prepare for those conversations.
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