The 5 Reasons Founders Fail — And the Fixes That Actually Move the Needle

The 5 Reasons Founders Fail — And the Fixes That Actually Move the Needle

What we’ve learned ourselves — and validated with dozens of founder clients across industries.

If you don’t know us: my business partner Mark Hasebroock and I have spent decades building, scaling, fixing, and investing in businesses across every industry you can imagine. DTC? Yes. Insurance? Yes. Trades? Yes. HR services? Absolutely. We’ve been inside enough companies to know exactly where founders get stuck — and why so many stay stuck far longer than they should.

And here’s the part nobody likes hearing:

Founders don’t fail because the market is tough. They fail because they repeat the same patterns that keep them small.

Every time. Every industry. Every revenue level.

The good news? Every single one of these patterns is fixable — and usually fixable faster than founders expect.

Let’s get into the five big ones.

1. Chasing Growth Without Protecting Cash

Most founders are addicted to topline. They love big numbers. They love saying “we’re up 40% year over year.” They love showing graphs that go up and to the right. But here’s the truth:

If you can’t protect cash, revenue is just a very expensive hobby.

Thirty-eight percent of startups die because they run out of cash. And almost 70% of Shopify stores never hit real profitability. Not because they didn’t grow — but because they grew blindly.

We worked with a founder doing $6M a year who was hemorrhaging cash. Her ads were “crushing.” AOV was up. But seven SKUs were losing money on every single sale. She wasn’t scaling; she was subsidizing her own customers.

Once we implemented a 13-week cash flow and SKU-level profitability review, she cut the losers, raised prices, renegotiated freight — and turned profitable in 90 days.

This is what protecting cash actually does: it tells you the truth before your bank account does.

Quick Framework: The Weekly Cash Clarity Trio

• A 13-week cash flow every Monday
  
  
• SKU-level profitability every week
  
  
• Contribution margin guardrails per channel
  
  

Your Next Controllable Step

Stop guessing. Build a simple 13-week cash view. It will show you exactly where the real problems are — and they’re never where founders think.

2. Treating Channels as Silos

I don’t care what industry you’re in — if your channels don’t talk to each other, your profits are leaking somewhere.

Founders run DTC over here, Amazon over there, wholesale “when we have time,” and service-led businesses are no better: brokers vs. field teams vs. online leads, all rowing in different directions.

This is why forecasting is a nightmare.
This is why inventory is wrong.
This is why CAC gets out of control.

Research backs it: siloed channels overspend by 25–40% and destroy forecasting accuracy. Meanwhile, companies with integrated strategies grow 3.5x faster.

One founder we coached had Amazon humming and Shopify bleeding. The two teams never even met. When we forced a unified weekly business review — one scoreboard, one plan, one set of KPIs — the entire business lifted. Shopify recovered. Amazon stayed strong. Inventory stabilized. That’s what integration does.

Quick Framework: The Unified Channel Model

• One company scoreboard
  
  
• One owner per channel
  
  
• One cross-channel demand review every month
  
  

Your Next Controllable Step

Create one weekly dashboard, pull all channels into the same meeting, and watch the clarity appear instantly.

3. Overestimating Marketing, Underestimating Operations

Founders LOVE marketing. It feels fun. It feels big. It feels like “we’re doing something.”
But let me be blunt:

Marketing cannot fix operational dysfunction. It actually exposes it.

Traffic is an amplifier — not a savior. More customers only increase the speed at which your operational issues punch you in the face.

Across industries, 72% of companies say ops is their #1 scaling barrier, not marketing. And nearly half of all abandoned carts come from slow or confusing shipping expectations, not price.

One founder we worked with spent a fortune on ads and creators while her backend was on fire — inventory constantly out of stock, a 3PL missing SLAs, customer service buried, and no forecasting rhythm. When we installed operational discipline — weekly scorecard, Level-10 ops meeting, replenishment cadence, SLA clarity — her CAC dropped and LTV shot up.

Not because she marketed better. Because she finally operated like a real CEO.

Quick Framework: The Operational Rhythm Pyramid

• A weekly 10–12 metric scorecard
  
  
• A Level-10 ops meeting every week
  
  
• A forecasting rhythm every 2–4 weeks
  
  

Your Next Controllable Step

Pick five ops metrics and track them weekly. When you start measuring ops, you start fixing ops.

4. Hiring Too Late (or Hiring Wrong)

Founders wait until they’re drowning before hiring. And when they finally do hire, they hire people who feel comfortable — not people the business actually needs.

This is how founders stay stuck in the weeds for years.
This is how businesses stall at $2M, $5M, $10M.
This is how burnout becomes the culture.

Companies that hire ahead grow up to 50% faster. But 60% of early hires fail because expectations are vague and roles are undefined.

One founder built a $4M company with a part-time ops helper and a friend doing social. It worked — until it didn’t. Once we built a two-year org chart and defined outcomes, he hired a GM and a marketing lead. Fourteen months later? $7.5M and a founder who finally felt like a CEO instead of a full-time firefighter.

Quick Framework: The 24-Month Org Design System

• A future org chart mapped two years out
  
  
• Three key outcomes per role
  
  
• A hiring filter based on capability, not comfort
  
  

Your Next Controllable Step

Write down the three things you personally do that the business absolutely cannot scale with. Those are your next two hires. Full stop.

5. Living in Vision, Starving Execution

Founders love vision. Founders love strategy decks.  Founders LOVE Painted Pictures.

But you don’t get points for dreaming. You get points for doing.

And this is where things fall apart.

Harvard Business Review found that 67% of strategies fail because no one executes — not because the strategy was wrong. Most founders don’t need more ideas; they need more discipline.

We worked with a founder who had a gorgeous Painted Picture — it belonged in a frame. But not one person on her team could tell us the top priorities for the quarter. There were no KPIs, no weekly check-ins, no scoreboard. The vision was excellent. The execution was nonexistent.

Once we implemented quarterly rocks, weekly check-ins, and a visible scoreboard, the momentum finally appeared. This is what founders don’t realize: execution is a skill — and it’s learnable.

Quick Framework: The Execution Engine

• Three quarterly rocks
  
  
• Weekly check-ins
  
  
• A visible scoreboard with owners
  
  

Your Next Controllable Step

Choose ONE quarterly priority, attach a weekly measurable to it, and track it religiously for the next 8 weeks.

Your Next Controllable Step (Overall)

If you recognized yourself anywhere in these five patterns, congratulations — you’re human. The founders who grow aren’t the ones who never make these mistakes. They’re the ones who stop making them on repeat.

Pick one area.  Install a simple weekly rhythm. Stick with it for 90 days.

That’s how you go from grit to growth. Not by working harder — but by operating smarter.

And if you want the unfiltered, behind-the-scenes version of these founder patterns — the ones most people are too polite to say out loud — Mark and I break them down every week on our podcast.

🎙️ Watch From Grit to Growth with Jennifer DiMotta & Mark Hasebroock on YouTube.
It’s operator truth without the sugar coating. And if you want something immediately actionable?

📩 Email me at jennifer@dundeegp.com
I’ll send you my Cheat Sheet for Balancing Growth and Cash — the exact framework we use with founders to stop “growing broke.”

When you learn to protect cash, design teams, integrate channels, and execute with discipline, your growth stops being accidental… and starts becoming inevitable.

About the Author

Jennifer L. DiMotta is the Managing Partner of Dundee Growth Partners, Founder of Uprisors, and a public company board member. She helps executives, founders, and leadership teams build profitable, scalable businesses by combining 25 years of corporate leadership experience at companies including Office Depot, Bluemercury, and Sports Authority with her expertise in strategy, financial discipline, and growth leadership.

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