Share Your Struggles
So much good comes from opening up when you're feeling down
Welcome to the latest entry in The Captain’s Log. You’re in good company with thousands of fellow entrepreneurs and innovators who have subscribed!
I’m your host, Bob, and my mission here is to share personal, behind-the-scenes stories of ups and downs from my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
If you’re the leader of any new thing—whether a startup, product launch or organizational change—odds are high that you’re struggling. Doing anything new is incredibly hard, mainly because individual humans and the companies and markets they occupy tend to keep doing what they’ve always done. Inertia is real—and hell.
If we’ve all experienced this, why don’t we discuss the struggle more often?
When friends, family, co-workers, investors, or long-lost connections ask us how our New Thing is going, we almost always reply with sunshine and rainbows. Inside, we’re struggling, and the people outside mostly know it’s a struggle. There are many reasons; mainly, we don’t want people to worry about us, and we don’t want negative perceptions that could hurt our ability to raise money or retain employees.
But sharing the pain might be the key to finding a breakthrough—if nothing else, in our sanity.
“I need a backup plan…”
It’s a weekday morning in summer 2019, and I’m in the office downing that first cup of coffee as I triage my inbox. I come across one of those out-of-the-blue messages that immediately earns my attention. It’s from a startup founder, Randy, whose company shares a lead VC investor with us. We met a year ago at a dinner where I shared the story of our acquisition and some of the trials and tribulations we survived to get there.
I guess my stories stuck in his mind as Randy got directly to the point:
”I'm thinking about backup plans should we fail to hit our growth objectives by EOY and be in a tough spot to raise more money. I want to be well-positioned to sell the business if that happens. I appreciated the story of how you thought about doing that and then executed your plans. Could I grab 30 minutes of your time in the coming weeks to discuss?”
Our companies are in entirely different industries and share almost nothing except this VC. But I know what he’s going through and immediately reply with my availability.
We hop on a phone call a few days later. Randy lays everything out in vivid color: He missed his sales goals again, his product upgrade got delayed, the bank account is dwindling, and his investors have signaled that there’s no way a Series B round is going to happen—and they aren’t sure they can put more money together in time. He’s stressed, struggling to keep the team focused, and starting to feel desperate. And he admits that he would never have reached out to me except that his VC nudged him to. It’s damn hard to admit you’re struggling.
Yep, been there.
I share more color from our company’s journey. I describe our decision to pivot the business or die trying. I talk about the multiple rounds of layoffs we did to buy time to find a new direction—and our back pocket plans to go to a skeleton crew of 5 people to keep the lights on if that failed. And I lay out how I approached potential acquirers who might come to the rescue if we got desperate.
But I mostly try and share the mentality that helped me lead our company through the struggle. I tell Randy about my decision to be incredibly open with our employees about our situation and the need for “all hands on deck” to survive. And how I pulled our COO, Ryan, in to become a trusted “pivot co-founder” to help shoulder the stress and share the highs and lows. We also got good at gallows humor.
Finally, I gave Randy credit for reaching out and admitting he needed help. I did this back in December 2015 when our company was struggling. Mostly, I was desperate for advice, ideas, angles, and intros. I got that, plus positive feedback on our business and team and the kind of unbiased encouragement that is more powerful coming from peers.
Randy seems buoyed by the end of our conversation. He asks questions here and there but mainly absorbs. He thanks me for my time, and I wish him luck…
It’s now four years later, and Randy’s company is still alive and looks to be in good shape. They raised the desperately needed money, new products are on the shelves (I even see them advertised on TV), and they’re hiring to power their expansion.
I have no idea if my half-hour of advice had any impact. Such butterfly effects are tiny and unpredictable. But if nothing else, I think my story helped give Randy a respite from the stress that helped him keep moving forward another day. And this only happened because he allowed himself to be vulnerable.
When You’re Down, Ask for a Lift Up
Leading a company in a new direction makes the job feel very personal. So when it’s struggling to succeed, you take it personally and feel like the company or project is a reflection on you. Those are the days when you pull the hoodie over your head and avoid any conversation where someone might ask, “How’s the business?” Nobody wants to admit they are failing, so we go dark.
But a funny thing happens when you admit the struggle and ask for help: You get it.
It’s human nature. Most of us are compelled to do something, anything, when a friend or even a complete stranger has stumbled. And we’re even more willing to assist when we see someone who has “put themselves out there” by taking a huge risk hits the wall.
People will lend assistance through ideas, experiences, and introductions. And just one lucky connection or insight can lead to a breakthrough.
Today, startups are struggling through a turbulent economy and shrinking investment market. Many companies will have to engineer an exit. But how will you find a buyer if you don’t share your situation? Founder/investor Hunter Walk recently advised companies to be more open in shopping themselves. The old saw “companies are bought, not sold” is often B.S. There are buyers out there—including me!—but it is very tough to see who is looking for a home because everyone’s afraid to talk about it.
If nothing else, talking about your challenges helps you get the pain out of your brain. It’s a shoulder to cry on in a society where everyone is supposed to be killing it. You’ll hear about others’ struggles and realize that maybe your situation isn’t as bad as it could be. And you’ll learn that if the whole thing crumbles, the only personal thing people will remember is that you had the guts to go for it and stuck to it for so long.
You don’t have to start by paying for special access or make ongoing commitments with a group like YPO or EO. Just go to the people who have lived what you’re living—the fellow founders, salespeople, client success leads, whatever—and ask for their advice.
Whatever tiny hit your ego takes will be eclipsed by the helping hand you’ll find in return.
How we might work together…
My team and I lead Hearty, a tech-enabled recruiting service that helps early-stage startups hire proven talent. Our senior team of repeat-exit founders sources and screens, saving you time and money. When you need help, let’s chat.
Feel free to schedule time together during my Open Hours for questions, feedback, networking, or any other topic.