(Don’t) Die on That Hill
There are many hills in entrepreneurship…but very few of them are worth dying on.
The staying power of machismo in entrepreneurship is daunting. Just recently, a colleague told an audience of fresh-faced founders that the best advice he’d been give was “never quit.”
Are you kidding me?
For years I nodded along as startup gurus lauded sacrifice and suffering. We regaled the youngins—-and ourselves—with slogans like ‘go big or go home’, ‘failure is fuel’, and ‘succeed or die trying’.
The net result was an entrepreneurial culture that downplays the concern of those who have no safety net, and glosses over how some people pay a higher price for failure than others.
Express a full range of emotion at your own peril lest you be labeled as lacking “toughness.” I was complicit in perpetuating this culture. It took a tragedy to dislodge me from it. Now, I feel compelled to call it out whenever and wherever I see it.
Entrepreneurship is hard, fraught with economic uncertainties. However, the idea that entrepreneurship is only for those with no fear and magical immunity to its economic and emotional consequences is wrong.
Pretending that “good” entrepreneurs don’t show emotions like fear isn't a Darwinian way to weed out the weak. It is preventing us from becoming strong. Unchecked, it could put American entrepreneurs on the endangered species list. And it is most certainly a barrier to more gender, racial and socioeconomic inclusion.
A few days ago, a founder navigating a very unpleasant event apologized after shedding a few quiet tears during a meeting. The founder apologized for having a brief and appropriate human reaction. If it is not a character failure to emote, why do we still feel sheepish when it happens?
Many who preach the “suffering makes you strong” gospel aren’t really suffering. If and when they did, few were burdened by racism or discrimination. Fewer lived on the edge of multigenerational poverty. They may mean no harm, but harm is still done.
My counter to the “never quit” doctrine is this: If you cannot succeed DO NOT DIE TRYING. Losing isn’t always winning. A failed business is recoverable. A broken life less so.
Caring for one's mental health can coexist with entrepreneurial ambition. Now that my eyes are open to it, I see it everywhere, including within myself. Toughness isn’t about persisting at all costs. Sometimes the toughest decision an entrepreneur can make is knowing when to shut it down.
In the last two years, I have radically changed the way I talk about mental toughness. I listen differently when founders share their fears. I think carefully before telling a founder to persist against all odds, especially when I have little insight into their personal circumstances. I talk about failure more frequently. I call out mistruths about what separates those who succeed from those who don’t. I make sure to point out that timing, luck, and robust access to resources often outweigh the impact of individual talent or skill.
There are things we all can do to change the conversation, and likely save a few lives in doing so:
We can create safe spaces for founders to find support and to support each other. We can proudly tell the stories we usually sweep under the rug–especially the ones that don’t glamorize protracted suffering. (Check out this one from my friend Ben Carcio).
If you are an ally or investor, pick up the tab. Next month, I am sponsoring a clinic for the female founders in our portfolio with a coach who specializes in teaching mental health self care for those who have little time to focus on it. Easy peasy.
What if community champions sponsored mental health support the same way they sponsor food, booze, and puffer vests? Could a city become the first to use mental health support for entrepreneurs as a cornerstone of their value prop? Yep.
AND, we can recognize some behaviors as warning signs, rather than heralding them as badges of honor or courage.
For this bit, I turned to my friend and psychologist Dr. Anna Lubiner. She suggest that some behaviors often celebrated in entrepreneurship are actually serious cause for concern:
1. Feeling Constantly Overwhelmed
No one can stay overloaded and overburdened without suffering the consequences. Being in a constant state of stress doesn't make you a stronger founder—it significantly raises the risk of severe burnout.
2. Experiencing Physical Symptoms of Stress
High-achieving people may ignore physical signs of stress, such as headaches, fatigue, insomnia, or digestive issues. These physical symptoms are warning signs that should not be ignored.
3. Becoming Emotionally Numb or Disconnected
When you start feeling detached or numb, burn out is a likely culprit. You may struggle to feel joy, excitement, or even sadness. This is not healthy for anyone over the long haul.
4. Productivity and Focus Are Declining
Founders are used to being productive, so when you notice that your focus, decision-making, or ability to concentrate is deteriorating, it may be a sign that you need recovery time or professional support to get back into a better place.
5. Engaging in Unhealthy Coping Mechanisms
Relying on alcohol, drugs, over-exercise or other behaviors to manage stress may signal that you're struggling to cope. Startup culture loves the “work hard, play hard” rhetoric, but being “hard core all the time” isn’t always the best way to recharge and recover.
6. Feeling Increasingly Isolated and Withdrawing from Support Systems
High achievers often isolate themselves when overwhelmed, feeling that they must solve everything on their own. Overtime, this isolation can make weathering tough times even harder.
7. Feeling Hopelessness
If you find yourself thinking that things will never improve, this is a significant sign of crisis. It is not a sign of weakness to ask for or offer help.
Above all, don’t go it alone. Here are three resources that Dr. Anna reminded me to share in this post:
National Suicide Prevention Lifeline (USA): 988
This is a 24/7 hotline that provides free, confidential support for people in distress. It’s also a resource for friends and loved ones to seek advice on how to help someone in crisis
Crisis Text Line
Text HELLO to 741741 (USA, UK, Canada) to connect with a trained crisis counselor via text. Contact emergency services or a crisis hotline immediately. Stay with them until help arrives or encourage them to call with you.
Changing the narrative around grit in entrepreneurship doesn’t mean we can’t celebrate hard work or learn from failure. We can do all of that while also acknowledging that not all struggle is created equal and that persisting at all costs often IS NOT the right decision.
There are many hills in entrepreneurship but very few of them are worth dying on.
(PS. Miss you JR. Always in our hearts as we fight the good fight in your honor.)
RevUp Capital Managing Partner Melissa Withers is a bullish advocate for innovating the ways in which new companies are funded and supported. Beyond building new economic models for early stage investing, Melissa is also committed to directing more entrepreneurial funding to those underserved and overlooked by traditional VC.
More About RevUp Capital
RevUp Capital invests in B2B and B2C companies that are revenue-driven and ready to double down on growth. We deploy cash and capacity to help companies grow from $1-3M to $10-30M, quickly and efficiently, using a revenue-based model. Companies enter our portfolio with $500K-$3M in revenue, a strong growth rate, and a team that’s ready to scale. Our typical investment range is $300K-$500K.
We invest into a company's market-facing activity using a cash and capacity model. We pair our cash investment with dedicated support from the RevUp Growth Platform: a powerful resource to build a data-driven growth engine, delivered by people who get the work done. Rather than take equity, companies return investment through a small percentage of revenue over time. More at www.revupfund.com