The 7 Deadly Sins of Startup Management: A Wake-Up Call for Small Business Owners
There’s something refreshing about being called out—gently, insightfully—on the ways we sabotage our own businesses. That’s what happened when I attended Leslie Fine’s talk at Startup Fest in Montreal. Her session, titled The 7 Deadly Sins of Startup Management, wasn’t just a list of dramatic metaphors. It was a mirror held up to every founder and business owner who’s ever burned out, overbuilt, lost focus, or chased growth at the expense of culture.
While the talk was clearly designed for startup founders, the insights landed hard for small business owners too—especially those of us wearing too many hats and juggling ambition with overwhelm. Here's a little summary with my own take on each “sin” and how I see them show up again and again in my work with local entrepreneurs. Let’s dive in.
1. Gluttony: Burning Cash Too Soon
We’ve all seen it—or done it ourselves: you finally get a cash injection (whether it’s a grant, a great launch, or a loan) and suddenly everything feels urgent. You upgrade platforms. You sign up for software. You hire. You say yes to a rebrand or that expensive photo shoot.
But most businesses don’t fail because they lack great ideas, they fail because they run out of money. According to CB Insights, 38% of startups fail because they run out of cash or fail to raise new capital.
Strategic advice:
If you’re in a growth phase, ask: Is this expense solving a problem that’s slowing revenue or scaling delivery? If the answer is “no, but it feels exciting,” pause. Build financial buffers, not just branding dreams.
2. Lust: Chasing Shiny Objects
New offers. New platforms. New partnerships. Small business owners are especially vulnerable to this—not because we lack discipline, but because we’re constantly bombarded with free content on social media showcasing the latest tools, trends, and “must-try” strategies for success. The real danger isn’t just distraction—it’s misalignment. Without the full context or a solid strategic foundation, jumping on every trend becomes a recipe for confusion, wasted time, and fragmented results. What looks like innovation can quickly become chaos if it’s not integrated with clarity and purpose.
A study by Kauffman Foundations shows that the average entrepreneur switches their business focus or strategy at least once in the first two years, often due to distraction more than data-driven decisions.
Strategic advice:
Every quarter, review your core growth drivers. If that new thing doesn’t directly amplify your mission or bottom line, it’s not innovation—it’s a distraction. Keep a “Someday Ideas” list so you can honor your creativity without hijacking your roadmap.
3. Sloth: Letting Urgency Slip Away
Sloth doesn’t look lazy. In fact, it often shows up as overwork without movement. When things are “fine,” we fall into routines that keep the business functioning but not necessarily growing. It’s when “just keep swimming” becomes a full-time job and nobody’s actually steering the ship.
As a business owner, you’re the one responsible for asking, “What’s the one move that would create real momentum right now?” If nobody is raising the stakes, entropy wins.
Strategic advice:
Block time each month to work on the business, not in it. Revisit your goals. Reassign tasks. And if you’re always stuck in the weeds, it might be time to hire—or ruthlessly simplify.
4. Envy: Comparing Your Business to Others
Envy doesn’t just trigger self-doubt—it muddies clarity. Suddenly, your strengths feel small and your original vision starts to bend. You shift focus, not because it’s right for your business, but because someone else made it look good. The result? Diluted messaging, scattered energy, and strategies built on someone else’s blueprint (what I like to call, creating a Frankenstein Marketing Strategy).
Strategic advice:
Shift your attention from imitation to differentiation. What makes your business distinctly valuable? What do your clients consistently rave about? That’s your edge—own it. Double down on what sets you apart instead of trying to keep pace with what others are doing.
5. Greed: Trying to Do It All Yourself
This one stings. Greed, in this context, isn’t about wanting money—it’s about hoarding responsibility. It's the founder who won’t let go of client onboarding, marketing, finances, and fulfillment. The belief that no one can do it “quite like me” is not only false—it’s fatal.
Delegation is the only way to scale. But more than that, it’s the only way to stay sane.
Strategic advice:
Identify your “Queen Bee Role”—the one thing only you can do. Everything else? Document, delegate, or delete. The longer you delay this, the harder it becomes to untangle.
6. Pride: Letting Ego Run the Show
Pride shows up in subtle ways: refusing feedback, overpromising to clients, making decisions based on what “looks good” instead of what’s sustainable. In sales, this can lead to misalignment—closing deals you’re not equipped to deliver on, or packaging offers to impress, not serve. Pride kills trust. And without trust, you can’t build anything lasting.
Strategic advice:
Ask someone you trust (a coach, a teammate, a client) to tell you the hard truth: Where is my ego getting in the way of effectiveness? Build a culture where asking for help isn’t weakness—it’s wisdom.
7. Wrath: Neglecting Culture
Wrath doesn’t have to be dramatic. It can look like resentment, tension, burnout, high turnover—or simply silence. When we stop prioritizing culture, we lose the human glue that holds everything together.
In one study by Deloitte, 94% of executives and 88% of employees agreed that workplace culture is important to business success , and yet, most small businesses don’t intentionally design it.
Strategic advice:
Even if you’re a team of one—or a team of five—make culture part of your business rhythm. How do you talk about values? Celebrate wins? Handle hard conversations? Culture isn’t a byproduct. It’s an operating system.
So… What Do You Do With This?
These seven “sins” aren’t just startup problems. They’re human problems. And if we’re honest, every business—no matter how values-driven or experienced—flirts with one or more of these on a regular basis.
But recognizing them gives us power. It gives us a language to name what’s not working, and a frame to shift into smarter, more sustainable leadership.
So here’s your invitation:
Run a “Deadly Sins Audit.”
Bring this list to your next team meeting—or pour yourself a coffee and do it solo. Ask:
Which of these is creeping into our business right now?
What small shift would move us in a better direction?
What do we need to protect or re-ignite?
Start by noticing what’s no longer serving you, then make one small move in a better direction.
