The Entrepreneur: Understanding Strengths and Weaknesses

By Michael D. Rubin, CEO & Founder · Updated September 2026 · 758 words

Entrepreneurs usually succeed on resilience, creativity, drive and energy, and they usually stall on impatience, distraction, drifting from plans and difficulty delegating. Knowing which traits you lean on most helps you build a company that runs well without you. That matters day to day, and it matters even more when you sell, because buyers pay for a company, not for the owner's personal effort.

Few owners have all the strengths or all the weaknesses. The useful exercise is to be honest about your own mix and to build a team around it.

The strengths that build companies

Most of these traits are the reason the company exists at all, and they deserve recognition before looking at the other side of the ledger.

• Resilience and a positive outlook. Setbacks become problems to solve rather than reasons to quit.
• Creativity and a tolerance for risk. New services, new markets and new ways of working usually start with the owner.
• Focus on goals. Clear targets keep a small company pointed in one direction.
• Organization. Many owners manage an extraordinary number of moving parts at once.
• Energy. Long hours and visible commitment set the pace for everyone else.

The weaknesses that hold them back

Each weakness tends to be the shadow of a strength, which is why owners so often fail to notice it in themselves.

• Impatience. Wanting results now can lead to rushed hires, underpriced jobs or abandoning a good plan too early.
• Distraction. Chasing every opportunity spreads time and money too thin.
• Reluctance to adopt new tools. Sticking with familiar systems can leave quoting, scheduling or accounting behind competitors.
• Drifting from the plan. Creativity without discipline wastes resources and confuses the team.
• Difficulty delegating. The owner stays the bottleneck, burns out and caps growth at the limits of one person's time.

How these traits show up in a sale

Buyers do not read a personality profile, but they see its effects. A company built on the owner's energy and creativity, with no one else making decisions, looks risky: what happens when that person leaves? Buyers respond by lowering the price, asking the owner to stay longer or tying part of the payment to future results. By contrast, a company where the owner's strengths have been turned into systems, a management team and a written plan looks like something a new owner can grow.

For companies with $3 million to $100 million in revenue, value most often falls between three and seven times adjusted EBITDA (earnings before interest, taxes, depreciation and amortization, with one-time and owner costs added back). Heavy owner dependence is one of the factors that pushes a company toward the lower end. What discount buyers apply when the owner is essential to daily operations goes into detail.

Turning weaknesses into a plan

The fixes are practical. Delegate one area at a time, starting with the one you enjoy least, and give the person real authority along with the responsibility. Many owners find it easier to write down how they make a decision before handing it over; the written version becomes the procedure the next person follows. Put the company's goals in writing and review them every quarter, so new ideas are weighed against the plan rather than replacing it. Update one outdated system a year instead of all of them at once.

Build a small group of advisors, such as your CPA, attorney and an outside mentor or peer group, who will tell you plainly when impatience or distraction is costing money. And measure the result: if the company had a better month while you were away, the plan is working.

What buyers reward

The owner traits buyers value most are the ones that have been turned into something that outlasts the owner. Creativity becomes a pipeline of tested services or products. Focus becomes a written plan with measurable targets. Energy becomes a sales team with its own habits. Organization becomes documented procedures for quoting, scheduling, purchasing and billing.

When the owner's personal strengths live inside the company in that form, a buyer can see how the business will perform after the owner steps back, and it pays for that confidence instead of discounting for its absence.

Where MDR & Associates fits

Our pre-exit consulting helps owners reduce dependence on themselves and build the management and systems buyers pay for, over the 12 to 24 months before a sale. Our founder, Michael D. Rubin, is the author of Sell Your Company for Maximum Value. When you are ready to see where you stand, request a free valuation snapshot.

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Questions owners ask next

How do I know if my company depends too much on me?

Imagine a two-week absence, or take one. List the decisions, customers and tasks that would wait for your return. If that list includes pricing, major customers, hiring or key supplier relationships, buyers will see dependence. Each item you move to someone else reduces the risk they price in.

Can an owner who loves the work stay on after selling?

Yes, and many buyers welcome it for a period. But a company that only works with you is worth less. The best position is a business that can run without you, where staying on is your choice and a point of negotiation rather than a condition of the sale.