3 Common Ways Entrepreneurs Think They’re Being Clever But Are Actually Being Idiots
Entrepreneurs have to be creative, but sometimes they take their creativity too far and it ends up backfiring in disastrous ways.
Confession time…
Back when I was a young, bro-y startup founder, I would write emails to people during the day but schedule them to be sent around 11pm. That’s how I’d email anyone ranging from employees, to customers, to prospective investors. In my warped, hustle-first mind, people would see these late emails, assume I was a harder worker, and be inspired by my dedication.
Fast forward 15 years, and I realize I was just creating unnecessary problems for myself.
When I sent late emails to employees, they’d feel pressure to respond in the middle of the night. This surely created the kind of resentment and burnout that caused job dissatisfaction, resentment, and high attrition.
When I sent late emails to customers, they’d assume I was willing to answer messages at all hours of the day, and they’d get annoyed if I didn’t respond to their requests within minutes regardless of the day or time.
And when I was sending late emails to potential investors, I was doing it because I thought it made me look like the kinds of hardworking founders they’d want to fund. In reality, my late emails were more likely getting lost in a flood of overnight emails that rarely got responded to.
As embarrassing as this confession is, I’m sharing it because I’m sure I’m not the only entrepreneur who’s ever thought I was being clever and sneaky when, in reality, I was just creating additional problems for myself. In fact, since entrepreneurs are always looking for clever workarounds, I’d even go so far as to suggest that most entrepreneurs are currently doing something they think is clever but is actually hurting more than it’s helping.
To help save you from yourself, here are the three most common mistakes I see entrepreneurs make where they think they’re being clever but they’re actually being idiots.
1. Asking for “advice” when you want something else
A few times a month I get emails from founders asking if I’d be willing to give them advice on their startups only to get into the meeting and immediately start getting pitched on something else. In those moments I immediately know they never really wanted my advice.
To be fair, I understand why this happens. Heck, when I was a founder I was often guilty of it, too. I’d regularly email potential customers and describe myself as a founder looking for feedback on a startup rather than someone trying to sell them something. And I’d do it because getting meetings was much easier when people thought I just wanted advice.
What I didn’t understand at the time was that being honest and direct with people is enormously important for efficiency. Specifically, when people clearly understand your intentions, they can quickly make decisions about whether or not to engage with you. In contrast, being deceptive can erode trust and permanently prevent any form of relationship from forming.
To be fair, the immediate result of this directness is that you’ll get more rejections, and — WARNING — those rejections aren’t going to feel good. But rejections are a gift. When someone quickly and clearly rejects you — whether it’s a prospective customer, prospective investor, or even a prospective romantic partner — you can quickly move on to a different prospect rather than wasting time chasing a person who’s going to say “no” once your intentions become more clear.
2. Making your company look bigger than it is
Picture this: you’re in a pitch or a meeting, and the question comes up, “Can your team handle this?” Suddenly, “we” becomes your favorite pronoun, and you’ve found yourself with an invisible army standing by your side.
You’re not alone. Plenty of us — myself very much included — have tweaked a pronoun or two to make our companies appear larger than we actually are. I remember lots of meetings where I toggled between roles, from CEO to software engineer, often within the span of a single conversation. I’d respond to feature requests with, “Let me consult with our engineering team,” knowing full well it was a one-person discussion.
But here’s what I’ve learned: this strategy rarely pays off. No customers ever chose to work with me because they believed I had a bustling office full of busy workers. On the contrary, the illusion often backfired. It set unrealistic expectations for support and turnaround times, leading to disappointment and eroded trust. In hindsight, embracing the reality of my startup’s size would have been far more beneficial, and it’s because authenticity breeds trust.
In the early stages of your startup, your genuine narrative is a powerful tool. It’s the story of an ambitious entrepreneur tackling the market head-on, and it’s what separates you from a faceless corporation. Your small size and dogged determination can forge stronger, more personal connections with your customers and partners. They’re not just investing in your product or service; they’re investing in you and your vision. That’s much more compelling and rewarding than being a tiny datapoint on some billion dollar corporation’s balance sheet. So don’t hide from your size. Use it!
3. Always “crushing it”
Founders are trained to give the impression that their startups are always on an upward trajectory. We’ve all heard the stories, seen the posts on social media, and likely even shared something ourselves where the message is a resounding, “We’re crushing it!” But here’s the reality: pretending everything is perfect when it’s not isn’t just dishonest — it can be downright destructive.
A facade of perpetual success prevents you from seeking the help you desperately need. After all, entrepreneurship is hard, and every founder knows the road is riddled with challenges. By admitting you’re facing difficulties, you open up opportunities for mentorship, advice, and support that could be instrumental in overcoming these hurdles. Remember that the startup ecosystem thrives on collaboration and mutual growth. By isolating yourself in a bubble of faux success, you’re missing out on valuable insights from those who’ve been in your shoes and navigated similar challenges.
Plus, investors and savvy stakeholders can see through the facade. Investors aren’t just betting on your current success; they’re investing in your potential to grow, pivot, and navigate the ups and downs of the startup world. By acknowledging the challenges you face, you demonstrate an understanding of your business’s realities and a strategic mindset geared towards long-term growth. This honesty builds credibility and trust with your investors, a group of people who already know that the path to success is rarely a straight line.
In other words, while it may be tempting to present an image of constant success, the reality is that acknowledging your startup’s challenges is not a sign of weakness — it’s a demonstration of maturity. So, the next time you’re tempted to say you’re “crushing it,” consider being honest about where you’re really at. It could be the most valuable decision you make for yourself and your startup.