The Freedom of Truth: Why Lies Cost More Than You Think
I have a friend who almost never lies.
Notice I said "almost."
I thought he was completely honest—one of those rare people who just tells the truth, always. Then two months ago, I caught him.
We were discussing his company's runway. Two months prior, he'd told me they had "18 months of cash left, comfortable position." Yesterday, he mentioned they're "about to run out, maybe 3-4 months max."
Both can't be true. The burn rate didn't 4x in two months.
So either he lied then, or he's lying now. Either way, the person I thought never lied... lies.
And here's what hit me: If someone who rarely lies still lies, what does that say about the rest of us?
The Pile-Up
When you start lying, the lies compound.
Lie #1 is easy to remember. You told Person A that Thing X happened.
Lie #2 gets tricky. You told Person B a slightly different version because the truth changed, but you need consistency with Lie #1.
Lie #3 is where it gets expensive. Now you're tracking:
- What you told Person A
- What you told Person B
- What actually happened
- What you'll tell Person C (who knows both A and B)
By Lie #10, you can't remember anymore. You've built an alternate reality that requires constant maintenance. One slip and the whole thing collapses.
What kind of life is that?
My friend caught himself in his own lie because he forgot which version he told me. The truth is simple. Lies require memorization.
The Founder Version
I've done this too. Not just regular lies—founder lies. The "strategic" kind. The "everybody does it" kind.
The partnership call lie:
We were talking to a lending partner for SimpleDirect Financing. They asked about our monthly volume—how many contractors we were working with, how much financing we were processing.
The truth: We had 20-30 active contractors, processing maybe $50K/month in financing applications.
What I said: "We're doing 80-100 contractors, processing $200K+ monthly."
Why? Because I was afraid the truth wasn't impressive enough. Afraid they'd pass. Afraid we'd lose the opportunity.
They partnered with us. Then we couldn't deliver the volume I promised. Of course we couldn't—I'd made it up.
Partnership cancelled within 6 months. Back to square one.
Except worse than square one: Because now we had a failed partnership on our record. Now we'd burned a relationship. Now the next potential partner would ask "Why did the last one end?"
All because I lied about numbers I should have just told the truth about.
What I Should Have Done
If I'd been honest: "We're at 25 contractors right now, processing about $50K monthly. We're growing 15% month-over-month. Our pipeline suggests we'll be at 50 contractors and $100K monthly in 6 months."
One of three things happens:
Outcome 1: They say yes anyway, because they see the trajectory and want to grow with us. Partnership works because expectations are aligned.
Outcome 2: They say no, because it's too early for them. We save 6 months of wasted effort on a partnership we weren't ready for.
Outcome 3: They say "Come back at $100K monthly and we'll talk." Clear milestone, we know what to build toward.
All three outcomes are better than lying and failing.
But I didn't do that. I was insecure. I was desperate. I was performing.
The Real Cost
The partnership failure wasn't even the worst part.
The worst part was what it did to me internally:
I stopped trusting my own judgment.
Because when you lie about your metrics, you can't use them to make decisions anymore. I didn't know if we were actually growing or if I was just lying better. I'd corrupted my own feedback loop.
I became paranoid.
Every call with the partner, I was terrified they'd ask for detailed data. Every meeting, I was calculating what I'd said before and what I needed to say now to stay consistent. The mental overhead was exhausting.
I couldn't ask for help.
When things weren't working, I couldn't tell advisors or mentors the truth. Because the truth would expose that I'd lied to the partner. So I just kept digging.
The lie didn't just cost me the partnership. It cost me my peace of mind, my ability to make good decisions, and my ability to get help when I needed it.
What kind of life is that?
The Pattern I See Everywhere
Once I started noticing this in myself, I saw it everywhere in the founder world.
The revenue lie: "We're at $50K MRR!" (Actually $15K MRR, but we project $50K if everything goes perfectly)
The traction lie: "We have 1,000 users!" (1,000 signups, 50 active users, but who's counting?)
The team lie: "We're building out the team!" (We made two offers that haven't been accepted yet, but it sounds good)
The progress lie: "Product is almost ready to ship!" (We're 60% done, but 60% sounds too honest)
The interest lie: "We're talking to several VCs!" (One intro call that went nowhere, but "several" sounds better)
Every single one of these is a founder trying to sound further along than they are. Trying to close the gap between where they are and where they think they should be. Trying to perform success until it becomes real.
I've told every one of these lies.
The Insecurity Behind It
Here's the uncomfortable truth: We lie because we're insecure.
When I exaggerated our partnership volume, it wasn't strategy. It was fear:
- Fear that we weren't good enough
- Fear that the truth would disqualify us
- Fear that we were behind where we "should" be
- Fear that everyone else was further along
- Fear that admitting the truth meant admitting failure
The lie was emotional insurance. If they rejected us, at least it wouldn't be because we were too small. I could tell myself "they would have said yes to our real numbers too."
But that's bullshit. And deep down, I knew it.
The Peer Pressure
The founder ecosystem amplifies this insecurity.
Every day on LinkedIn:
- "Excited to announce our Series A! 🚀"
- "We're hiring! Join our rocketship! 💪"
- "Just crossed 10,000 users! 🎉"
- "Featured in TechCrunch! 📰"
Nobody posts:
- "We're almost out of money and I'm scared"
- "We lost our biggest customer today"
- "I have no idea what I'm doing"
- "We're probably going to shut down"
So you see everyone winning (performing wins) and assume you're the only one struggling. Which makes you lie about your own progress to keep up.
The pressure to perform becomes the pressure to lie. And once you start, it's hard to stop.
The Turn
I can pinpoint the moment things changed for me.
We were sunsetting SimpleDirect Financing—the product I'd lied about to the partnership. It had failed. We were shutting it down.
Old me would have:
- Quietly killed it
- Not mentioned it publicly
- Pivoted the story to something else
- Pretended it never happened
Instead, I wrote a blog post: "Why We're Sunsetting SimpleDirect Financing."
Laid out the numbers. Explained what didn't work. Shared what we learned. Posted it publicly.
The response shocked me.
Not judgment. Not mockery. Not "I told you so."
Relief.
Other founders messaged me: "Thank you for being honest about this. I'm going through something similar and felt like I was the only one."
Investors reached out: "This kind of transparency is rare. Let's talk about what you're building next."
Customers understood: "Appreciate you being upfront. Still using your other products."
The honesty didn't hurt me. It helped.
Where I Am Now
I'm honest about where I am now. Not perfectly honest—I'm still working on it. But dramatically more honest than I was.
When a product isn't working: I say it publicly. SimpleDirect Financing sunset post. SimpleDirect Desk slow adoption post. No hiding.
When revenue is down: I share it on my podcast. Explain what we're doing about it. Don't inflate the numbers.
When I don't know something: I say "I don't know" instead of making something up.
When someone asks about metrics: I give them real numbers, not projections dressed up as actuals.
Is this scary? Yes. Does it feel vulnerable? Absolutely.
But here's what I've gained:
Peace of mind. I don't have to remember what I told whom. The truth is the same for everyone.
Better decisions. When I'm honest about metrics, I can actually use them to guide strategy.
Real help. When I tell people the truth, they can give me real advice. Not advice based on the fake version I presented.
Authentic relationships. The people who stick around after I'm honest are the people who matter.
Freedom. I can say what's actually happening without calculation or fear.
The Irony
Here's the most ironic part of all this:
I became an entrepreneur for freedom.
Freedom to work on what I want. Freedom to build what matters. Freedom from corporate politics and performance reviews and pretending to care about things I don't.
But by lying about my progress, I built my own prison. I had to maintain the lies. I had to perform constantly. I had to pretend everything was great when it wasn't.
I escaped corporate performance theater just to create founder performance theater.
It took me six years to realize: Being authentic is the only way to be free.
The lies pile up. The maintenance becomes exhausting. The fear of being caught becomes paralyzing.
But the truth? The truth is simple. The truth is consistent. The truth doesn't require memorization or calculation or fear.
The truth is freedom.
What Changed
Where I am now is not spectacular. Not impressive by Silicon Valley standards. Not TechCrunch-worthy.
SimpleDirect has three products. Two are doing okay. One we sunset. We're profitable some months, not others. Revenue is growing, but slowly. Team is tiny. No funding. No press. No conference speaking invitations.
But I enjoy what I do.
And isn't that ironic? It took me six years to get to do what I actually wanted. Six years of lying and performing and trying to impress people before I realized:
The whole point of being an entrepreneur was to work on things I'm passionate about.
Not to raise the most money. Not to grow the fastest. Not to get TechCrunch articles. Not to impress other founders.
Just to build things I care about, with people I respect, in a way that's sustainable.
I could have had that from day one if I'd just been honest about what I wanted.
The Questions You Should Ask
What are you lying about right now?
To partners? To investors? To customers? To other founders? To yourself?
Write it down. Be specific. No judgment, just honesty.
Why are you lying?
Is it fear? Insecurity? Peer pressure? Desperation? All of the above?
Understanding why helps you address the root cause instead of just the symptom.
What's the worst that happens if you tell the truth?
Usually, it's not as bad as you think. And the relief of not maintaining the lie is worth it.
What would it look like to be honest starting today?
Not confessing every past lie. Just committing: from today forward, I tell the truth.
The Practice
Being honest isn't a one-time decision. It's a daily practice.
When someone asks how it's going: Tell them the truth. Not "crushing it!" if you're not crushing it.
When you're tempted to inflate numbers: Don't. Give real numbers with context.
When something isn't working: Say it. Don't hide behind vague optimism.
When you don't know: Say "I don't know" instead of making something up.
When you make a mistake: Own it immediately. Don't wait for someone to catch you.
It's uncomfortable at first. Every time you tell the truth when a lie would be easier, there's a moment of fear.
But that fear gets smaller. And the freedom gets bigger.
The Permission You Don't Need
You don't need permission to stop lying.
Not from investors. Not from partners. Not from other founders. Not from LinkedIn. Not from me.
You can just... stop.
Start telling the truth today. About your metrics. About your progress. About your challenges. About what you actually want.
The worst case? Some people are disappointed that you're not as far along as they thought.
The best case? You build a reputation for honesty that becomes impossible to fake and valuable beyond measure.
And the middle case—the most likely case? Nothing changes externally, but everything changes internally.
You sleep better. You think clearer. You make better decisions. You get real help. You build authentic relationships.
You're free.
What I'd Tell My 2019 Self
Stop lying about the numbers. The truth is less impressive but more useful.
Stop trying to sound further along than you are. The gap between performance and reality just creates anxiety.
Stop thinking everyone else has it figured out. They're lying too.
Be honest about where you are. People respect honesty more than inflated metrics.
And here's the thing you won't believe until you experience it: The authenticity becomes your competitive advantage.
In a world where everyone is performing, the person telling the truth stands out.
In a market where every founder is inflating their metrics, the one sharing real numbers builds trust.
In an ecosystem where failure is hidden, the founder who openly shares what didn't work becomes someone people want to learn from.
Authenticity is the only remaining moat.
Everything else can be copied. Your product, your marketing, your strategy, your positioning.
But your specific experience—the actual truth of what you've built and learned and failed at—that's yours alone.
The Bottom Line
My friend who almost never lies still lies. Because the pressure to perform is real. The fear of judgment is real. The insecurity is real.
But the cost of lying is higher than the cost of truth.
The lies pile up. The maintenance becomes exhausting. The fear of being caught becomes paralyzing. The internal corruption makes good decisions impossible.
And for what? To impress people who don't matter? To maintain a performance that everyone sees through anyway? To delay the inevitable moment when reality catches up to the story?
What kind of life is that?
The truth is simpler. The truth is consistent. The truth doesn't require memorization or maintenance or fear.
The truth is freedom.
And if you're an entrepreneur who started this journey for freedom—freedom to work on what matters, freedom to build what you care about, freedom to live how you want—then lying is the opposite of what you're trying to achieve.
Being authentic is being free.
The lies pile up. The truth stays simple.
Choose freedom.
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