The Two Things Founders Want Most (But Rarely Ask For)
Running a company is one of the most rewarding things you can do, but also one of the loneliest.
Over the last 15 years, I’ve met with more than 120 founders. Different industries, different goals, different business models. But again and again, two needs come up more than any others:
Founders want someone in the foxhole with them
Founders want honest, unbiased feedback
Not revenue. Not strategy decks. Not clever hacks.
They want someone to stand beside them through the storm, and someone they can trust to tell them the truth.
Let’s unpack why these two things matter so much, and what you can do about it if you’re feeling the weight yourself.
It’s Lonely at the Top (And Founders Feel It Deeply)
Being a founder often means being afraid to speak freely to the people around you.
You hold back with your executive team because you don’t want to shake their confidence.
You hold back with your board because you don’t want to risk losing their trust or triggering concern.
You hold back with your partner at home because you don’t want to worry them.
And so the weight builds.
You’re carrying the future of the company and the burden of worry—alone.
I’ve lived this myself. I remember a particularly stressful stretch of months where I truly feared that the company I was running could collapse. My board was strong—but they were scared too. I had to be careful with what I shared. I ended up walking for hours every day just to clear my mind and come to terms with reality.
Looking back, an advisor would have been a godsend. I had one prior, but he’d stepped back to run for elected office. That gap made everything harder.
As an aside: while we grow Founded Partners, I now work with an advisor and coach of my own. Practice what you preach.
The Emotional Cost of Isolation
This kind of loneliness doesn’t just feel bad—it impairs performance.
Research in business psychology shows that isolated leaders tend to ruminate more, make slower decisions, and experience higher levels of burnout and anxiety. When you don't share thoughts or concerns, you limit your ability to process them. Talking helps regulate emotion and improve cognitive clarity (Pennebaker, 1997).
At a time when decisions are urgent, you can’t afford to be stuck in your own head. But many founders are.
Why Founders Can’t Always Talk to Their Team or Board
Let’s be clear: it’s not about a lack of support. Many founders have strong teams and engaged boards. But those relationships come with dynamics you need to manage.
You can’t always speak openly to your board because if confidence in your leadership erodes, you can be replaced.
You can’t always be fully honest with your executive team because they take cues from you. Share too much fear, too casually, and you can introduce instability.
I always advocate for openness, honesty, and overcommunication when there’s an issue. But how you communicate it—and who you speak to—matters.
What Founders Really Mean by “Someone in the Foxhole”
At Founded Partners, we use the phrase “someone in the trenches with you.”
It means:
Someone who’s done it before—not just someone who’s smart, but someone who’s been where you are and lived to tell the tale.
Someone who’s rolled up their sleeves—who isn’t afraid to get into the details with you.
Someone who’s accessible—you can text or call without waiting for a formal booking.
This is the kind of support founders need—but rarely find.
Why Co-Founders Aren’t Always Enough
Co-founders matter—a lot. They bring energy, shared ownership, and often deep alignment.
But they’re not advisors. And those relationships take work to maintain, especially as the company grows and roles shift.
Sometimes co-founders grow at the same pace. Sometimes they don’t.
Sometimes they stay focused. Sometimes they get distracted by other projects—or life.
And often, one co-founder ends up rotating through roles like COO, CFO, and eventually… “Chief Strategy Officer”—the title you give someone when you don’t quite know where they fit anymore.
We need to get better at replacing co-founders who no longer scale with the business.
And we need to make space to navigate co-founder dynamics before they become problems.
That’s part of what Founder Advisory is built to support.
Why Honest Feedback Is So Hard to Get
The second thing founders crave—almost as much as connection—is unbiased, unfiltered feedback.
And again, it’s hard to get that from your board or team. Everyone’s got skin in the game. Everyone’s protecting something—reputation, position, equity, perception.
Without real feedback, founders can get stuck in their own assumptions—or worse, stall at critical moments.
As an advisor, I give honest feedback by starting with deep listening. The first move is always to let the founder talk—vent, share, lay it all out. Then I repeat back what I’ve heard, ask questions to clarify what’s really going on, and offer advice that’s direct but constructive.
I do this with confidentiality—and confidence. Founders can trust me because I’ve been through it myself. That’s what makes it safe to be honest.
I challenge founders all the time. Sometimes it lands right away. Other times it takes weeks or months to shift their thinking. That’s okay. Founder Advisory isn’t a one-off—it’s a relationship.
What Founder Advisory Actually Looks Like
Founder Advisory is a mix of strategy, psychology, and presence.
It’s virtual, ongoing, and always high-access.
We meet at least once a week—sometimes twice
I join strategic or governance calls when needed
Founders text or call throughout the week as challenges arise
Some days the calls are pure strategy.
Other days even the most type-A founders break down and need space to just feel and share.
It’s a fine line. But that’s the whole point.
We support the person leading the company—because if they’re not okay, nothing else will be either.
This Is Not Coaching. And It’s Not Consulting.
Executive coaching tends to focus on personal development. Traditional consulting tends to focus on business mechanics.
Founder Advisory blends the two.
It’s for founder-led, lower middle market companies with $5M–$50M+ in annual revenue—leaders who are scaling, hiring, fundraising, exiting, or reinventing.
We’re here to help you move fast, stay clear-headed, and make decisions that build momentum—not just put out fires.
The founders who benefit the most are ambitious, reflective, and self-aware enough to know they don’t want to do it alone.
The Best Feedback I’ve Ever Received
The most meaningful feedback I’ve ever received from a founder?
“I’m waking up excited for the day again.”
That means they’re clear. Grounded. Focused. Not running on anxiety or pressure, but purpose.
That’s what good advisory can do.
If You’re a Founder Reading This
Find an advisor.
Someone who’s done what you want to do.
Someone you trust.
And then—share. Don’t keep it all in.
This job is too hard to do alone.
If you’re ready for support or even curious what that could look like, let’s chat - you can book 30 minutes with me here.