Founders Who Wait Fail
Every January, founders tell me what they're going to fix this year.
"I need to hire someone for sales."
"I'm going to deal with that problem client."
"I need to finally get serious about financial systems."
Then February arrives. March passes. By summer, nothing has changed.
I've learned something working with hundreds of founders. The gap between knowing what needs to be done and actually doing it is often where businesses succeed or fail.
Waiting feels safer than deciding. But in business, waiting is rarely the right answer.
The Lesson My Grandfather Taught Me
As the old saying goes: 'The best time to plant a tree was 20 years ago. The second best time is now.
My grandfather, a US Army officer, fought in World War II and later built a successful business. He told me something I'll never forget:
"In combat and in business, waiting is rarely the right answer. You take all the data and insights you have, make a decision, and move forward. If you're right 51% of the time, you're still going to succeed because you'll either learn from it, fix it, or adapt. But if you just sit there and wait, bad things are going to happen."
He was right. You can adapt and improvise. You can overcome challenges. But you can't do any of that if you're standing still.
Why Founders Wait
I've watched this pattern play out over and over. A founder knows exactly what needs to happen. We've talked through it. They've seen the data. The path forward is clear.
Then they wait.
Sometimes it's ego. "I should be able to handle this myself." Sometimes the problem seems too big; when you're staring at the whole elephant, it's easier to do nothing than to take the first bite. Or there's fear of making the wrong choice, so they make no choice at all.
In my own business, I waited years to bring someone on for business development. Why? Part ego, part fear, part convinced I should handle it myself.
That delay cost me. The business could have grown faster. Deals that should have closed sat untouched. Relationships that should have been built never happened.
That's the cost of waiting.

When Founders Finally Stop Waiting
Don Spies, founder of Outrider Analytics and a veteran I recently had on the MilCom Founders Podcast, said something that stuck with me:
"There is an inherent fear to start something like this. When you step forward and say, ‘I'm going to start a business,’ there is this inherent fear. But once you get over that fear, having the personal courage…when you take that step, what blew my mind was the number of doors that opened up."
The hardest part is making the decision and taking action.
I challenged a founder once who kept hitting walls with lenders. I told her: "Get 10 prepaid contracts. Prove the model, then come back."
She was frustrated. "That's going to take forever."
45 days later, she came back with 25 pre-signed contracts covering the first two months of service.
Suddenly, financing options opened up. Not because the business fundamentally changed. Because she stopped waiting and started proving her concept.
Another founder wanted $500,000 for a brewery concept. Instead, I helped him secure a much smaller loan to test the model. After validating customer demand, he was able to scale successfully.
The difference? He moved from waiting to testing. From theory to proof.

The Three Decisions Founders Wait Too Long to Make
- Hiring (or Firing)
You know you need a sales leader. You know that team member isn't working out. You know your operations need someone who actually understands systems.
But you wait because:
- Finding the right person takes time
- Letting someone go is uncomfortable
- You don't have the bandwidth to train someone new
- Maybe they'll improve on their own
Meanwhile, your business suffers. Revenue stays flat because you're doing work you shouldn't be doing. Problems compound because you're keeping people who shouldn't be there.
Ready Founders™ make the hire or make the cut. They know the cost of waiting is higher than the discomfort of deciding.
- Dealing with Bad Clients
You've got a client who pays late, demands unreasonable changes, and drains your team's energy.
But you wait because:
- They're revenue
- You don't want conflict
- Maybe they'll get better
- You're worried about the gap they'd leave
Meanwhile, your team is miserable. Your good clients get less attention. Your profit margins shrink because this client requires triple the work.
Ready Founders fire bad clients. They know that protecting their team and their business model matters more than holding onto difficult revenue.
- Building Financial Systems
You know you need better visibility into cash flow. You know your current reporting isn't giving you what you need to make decisions. You know your tax strategy is probably costing you money.
But you wait because:
- It feels overwhelming
- You're not sure where to start
- You're too busy running the business
- It's not urgent until it suddenly is
Meanwhile, you're making decisions blind. Missing opportunities. Paying more in taxes than necessary. Running closer to the edge than you realize.
Ready Founders build systems before they desperately need them. They know that financial clarity creates options.
The 51% Rule

The truth about decision-making? You don't need perfect information.
My grandfather was right. If you make decisions and you're correct 51% of the time, you're still moving forward. You're learning. You're adapting. You're building momentum.
But if you wait for perfect clarity, you're guaranteed to be left behind.
Making a decision with 70% certainty might lead to success or failure. Waiting for 100% certainty guarantees missed opportunities.
The market doesn't wait. Your competition doesn't wait. Your best people won't wait forever for you to make the hard calls.
Start Small, But Start Now
Reid Hoffman, founder of LinkedIn, famously said: "If you are not embarrassed by the first version of your product, you've launched too late."
The same principle applies to every decision you're avoiding.
If the decision feels too big, break it down.
Don't know if you should hire a full-time salesperson? Start with a fractional hire or a contractor.
Can't fire a whole team at once? Start with the person who's clearly not working out.
Don't know how to build complete financial systems? Start by pulling your P&L and balance sheet monthly instead of quarterly.
You don't need to solve everything at once. Just stop waiting and start moving.
My Challenge to You This January
Write down the three decisions you've been avoiding.
Pick the clearest one, the decision where you already know what needs to happen.
Give yourself 48 hours to make the decision and take the first action step.
Not "think about it more." Not "gather more information."
Make the decision. Take action. Then adapt as you learn.
Because the cost of waiting is always higher than you think.
Ready Founders know this. They make decisions when they have enough information, not perfect information. They understand that momentum beats perfection.
Don't let another year go by with the same problems you identified last January.
Stop waiting. Start leading.
Ready to stop waiting and start building the systems your business needs? Take a Ready Founder Assessment to identify exactly where to focus first.
The Ready Founder™ is part of One Degree Financial's commitment to helping founders gain the financial clarity and confidence they need to scale and exit successfully.
Ready to close the year with clarity? Let's talk about building your enterprise value plan for 2026. Schedule a conversation.
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About the Author: Rod Loges is CEO of One Degree Financial and host of the MILCOM Founders podcast, where he helps veteran entrepreneurs build businesses with strong financial foundations.