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When I asked a group of founders recently what they really needed, their answer surprised me.
They didn’t say funding.
They didn’t say marketing help.
They said, “We need people to tell us the truth.”
And as a founder who’s also a mentor, I get it.
Because somewhere along the way, we confused being supportive with being relentlessly positive. In too many startup conversations, the default has become cheerleading. We tell founders, “You’ve got this!” or “It’ll all work out!” when what they actually need is someone to say, “That math doesn’t work,” or “Your model needs to change if you want this to survive.”
That’s the truth nobody tells you.
Culture of relentless positivity
In many of the smaller ecosystems where I’ve worked (including my home state of Arizona), this dynamic is amplified. We don’t have startups on every corner. We have a limited but growing group of brave founders building the future.
We genuinely believe that the next breakout success could be sitting in our own backyard.
And as a community, we want to nurture them.
So we hesitate to highlight the flaws, to tell the whole truth, to point out that the dots aren’t connecting.
After all, no one wants to be the person who told the next big thing, “That’s not going to work.”
I’ve been guilty of this myself. Recently, I was part of a mentoring program for a local pitch competition. One of the finalists was building a mobile app without a product in market yet, but was talking about raising capital for AI development and untested go-to-market activities. I asked a couple of gentle questions, but each answer revealed more holes in the story instead of deeper expertise about what the business actually needed.
The competitive landscape was crowded. Customer conversations hadn’t revealed a clear buying trigger yet. A compelling advantage that would justify immediate investment wasn’t clear.
But I—along with the other mentors in the room—defaulted to cosmetic feedback.
“Less text on your slides.” “Break the story down differently.”
We had limited time, other companies to see, and no one wanted to start the conversation that really needed to happen. Eventually, the organizer asked the company to step down from the competition. I offered to spend more time with the founder one-on-one afterwards, but they never reached out.
This story repeats itself over and over in our ecosystem. And generally, the entrepreneur is the last to know (if they ever do).
Mentoring is not as easy as it sounds
I’ve been mentoring founders for more than a decade, and I’ll be honest: it’s one of the hardest things I do.
Not because I don’t care. I care deeply. But because giving truly useful advice requires something specific to work with.
When a founder comes to me with vague concerns, “Things aren’t growing like I hoped,” or “I’m worried about cash flow,” I find myself defaulting to generalities. I offer encouragement. I share patterns I’ve seen. But without concrete numbers, without a clear picture of their model, I can’t tell them what options they have to improve their situation.
And that’s frustrating for both of us.
The difference a plan makes
The most productive mentoring conversations I’ve had all have one thing in common: the founder shows up with a concrete plan.
Not a pitch deck. Not a vision board. A real plan with numbers, assumptions, timelines, and trade-offs spelled out.
When I can see that a founder expects to hit $50K MRR in six months but their marketing channels and conversion rates make that mathematically impossible, I can point to the specific problem. When their burn rate and runway don’t align with their growth projections, we can address it directly.
Suddenly, I’m not guessing about what the problem is or hedging my advice about where they should focus. I can say, “Here’s what needs to change, and here are a few things I’ve seen work.”
That’s the mentorship founders actually need. And frankly, it’s the mentorship I want to give. But I can only do it when founders come prepared with something real to examine.
Without that foundation, even the best-intentioned mentor ends up saying “Looks great!” when what the founder really needs to hear is “Something’s not adding up, let’s figure it out together.”
Why honest conversations are so hard to have
Founders coming unprepared is one part of the problem, but there’s something mentors struggle with, too.
The truth is, delivering hard feedback as a mentor is genuinely difficult for a few reasons.
#1: Time is always the enemy. Whether I’m volunteering at a pitch competition with four companies to see in one day, or squeezing in a mentoring call between client meetings, I often don’t have the luxury of opening a difficult conversation. These discussions take time: time to build trust, time to work through defensiveness, time to explore alternatives.
When you’ve got ten minutes before your next meeting, “less text on your slides” is a lot easier than “I’m not sure this business model works.”
#2: The emotional labor of hard conversations is real. You have to gauge how much truth someone can handle and what they really want to do with their business. I once had a one-on-one conversation with a founder who asked for my unvarnished opinion. So I shared my honest assessment: they needed proof of concept before seeking funding, not the other way around. As we brainstormed some creative ways to validate their idea without capital, they got angry, accused me of trying to take advantage of them, and disconnected the call.
That experience sits with me. I hate that this person felt my feedback was personal or motivated by anything other than wanting to see them succeed.
But it makes me wonder: should I even start these conversations?
#3: Nothing happens in a vacuum. Ecosystem dynamics matter, especially in a tight-knit community. When you see the same companies at multiple events, when mentors are volunteering their time in exchange for visibility, when no one wants to be the person who “crushed someone’s dream,” there’s an enormous pressure to stay positive. Add in groupthink (no one wants to be the first to express a critical opinion), and you end up with rooms full of experienced people giving surface-level feedback because it’s safer.
So we stay on the surface. We give founders encouragement when what they need is a reality check.
Why truth matters
Remember those founders I mentioned at the beginning? The ones who said they needed people to tell them the truth?
They were right to ask for it. Because when everyone around you is positive, it’s easy to mistake encouragement for evidence. You start making decisions based on what other people hope will happen, not what’s actually likely.
And that’s dangerous.
Building a business is already risky. But when you add layers of misplaced optimism and incomplete advice, you’re compounding that risk.
Entrepreneurs deserve better.
My desire to reduce business failure rates as well as my frustration as a mentor—the lack of time, the missing details, the difficulty of having honest conversations— is exactly why we built Fric.
I wanted a tool that helps everyone involved—founders, team members, mentors, advisors—see what the founder actually believes about their business, so advice can be better tailored to the real situation.
This was so important that we literally built a feature called Reality Check. You enter your best assumptions (your sales, costs, goals) and Fric shows you whether you can actually make money based on those numbers. If not, it shows you how much capital you’d need to raise or how much more you’d need to sell.
It’s not about criticism. It’s about clarity.
Because there’s always more than one path to success.
The challenge is figuring out which one is right for you.
The kind of ecosystem we need
Founders don’t need more cheerleaders. They need people and tools that help them see reality so that they can shape it.
As an ecosystem, we have to get more comfortable with honest feedback, even when it’s uncomfortable to give and hear. That means creating space for deeper conversations, rewarding candor over politeness, and prioritizing business fundamentals over pitch performance.
Because when you can see what’s real, you can make better decisions. You can change course before you run out of time, money, or energy.
The truth might not always feel good in the moment, it’s the only thing that gives you a real shot at success.
So here’s my invitation:
If you’re a founder who’s tired of cheerleading and wants someone to tell you the truth, both as a person and through tools that show you the reality of your numbers, join us at Fricin Plan Fridays at 9:00 a.m. MT, here’s the link. I promise we’ll have an honest conversation about what’s working and what needs to change.
If you’re a mentor, advisor or ecosystem leader who’s felt this same frustration, let’s talk about how we can do this better together.
And if you’re an entrepreneur who’s gotten real, honest feedback that changed your trajectory, tell me how they did it. I’d love to hear what works in these crucial conversations.
Because the more we normalize truth-telling in our ecosystem, the better our chances of building businesses that thrive.
That’s what every entrepreneur deserves.
Ready to move from insight to action? Fric helps you build a plan rooted in reality. It connects assumptions, actions, and actual results so you can see what is really driving cash and profit. Start a free two-week trial and explore Fric at your own pace.
Stephanie Sims is a recovering investment banker, two-time founder, speaker, venture capitalist, and startup educator who believes every entrepreneur should build a business that makes dollars…and sense. She is also the author of Funding Your Business Without Selling Your Soul. After watching too many promising founders chase funding at the expense of long-term success, she created Fric —an interactive platform that turns your big vision into actionable steps. Fric helps entrepreneurs like you map and navigate the shifting path toward the world you believe should exist. This skill, which Fric calls visionary prowess, equips you to make confident decisions, take committed action, and chart your own route to success.
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