Chapter 4: The Business Plan
Plan, Execute, Iterate
business plan, execution, iteration, planning, strategy, entrepreneurship
Because of my background in accounting, finance, and economics at Tech — and because I spent several years doing business development before I ever started a company of my own — I became the business-planning guy wherever I went. It wasn’t a title anyone gave me. It was just a pattern: walk into a new situation, and pretty soon someone would hand me a yellow legal pad and say, “You do the plan.”
I’ve written a lot of plans. I’ve also seen a lot of plans fail, and I’ve learned that the plan itself isn’t what saves you. The discipline of planning is.
The Five Puzzle Pieces
When I think about putting a plan together — whether you’re starting something from scratch or remaking something that’s already running — there are five pieces that matter above everything else. People. Market. Idea. Finance. Exit.
Everything else is important, sure, but those five are the load-bearing walls. Miss any one of them and the whole structure is shaky.
People are who you’re doing this with — your team, your partners, your advisors. Market is who you’re selling to and how big that universe really is. Idea is the thing you’re building, and whether it actually solves a problem someone will pay to have solved. Finance is the money: where it comes from, where it goes, and whether the math holds together. And exit — we’ll come back to exit, because most people skip it and they really shouldn’t.
The rest of what goes into a plan — operations, marketing channels, competitive landscape — matters, but if you get those five right, you can figure out the rest. If you get them wrong, no amount of polish on the other sections will save you.
A Plan Is a Living Thing
Here’s the mistake I see people make with business plans: they treat the document like an assignment. You write it, you turn it in, and you’re done. That is not how this works.
A plan is iterative. You write a draft, you sit down with people who know the space — mentors, advisors, someone who’s actually been in that industry — and you get their honest reaction. Then you go back and update it. You start the business. You see what’s actually happening versus what you projected. You update it again.
The boards of directors I worked with met monthly. We reviewed our plan at least annually — sometimes we rewrote it entirely, depending on how much had shifted. That wasn’t a sign of failure. That was how you stayed honest about the business you were actually running versus the one you’d imagined.
Don’t try to write the be-all, end-all business plan on your first attempt. There’s no extra credit for length — in fact, I’d argue you get marked down for it, because nobody wants to read a document that buries the important things in filler. What you want is concise: your market (and how you’ve really studied it), your pricing, who’s managing the business and with you, and what your significant milestones are. Start there. The rest you iterate into over time.
A Good Plan Is a Good Story
Here’s a thing I’ve come to believe deeply: a good plan is, at its core, a good story. And one of the most valuable skills you can develop while you’re still in school is the ability to tell that story in front of a room.
Public speaking. Presentation skills. I know that sounds like career-services advice, but I mean it structurally. If you’re going to be an entrepreneur, you are going to be telling this story constantly. You’ll tell it to prospective employees to get them to join you. You’ll tell it to your market to get them to buy. You’ll tell it to bankers, to potential partners, and if you’re heading toward a sale — to private equity, to venture capital, to a bigger company that might acquire you — you’ll be telling that story over and over again until the words are completely second nature. You don’t just want to know your plan. You want to be able to perform it.
And like any good story, the plan needs an ending.
The Part Everyone Skips: Exit
One of the biggest mistakes I made in my entrepreneurship career was not being aligned with my CEO on exit. We’d built something real — a business worth building — but we had never had a direct conversation about what we were actually going to do with it.
My goal from the beginning was to exit. I didn’t care much about the specific mechanism — venture capital, private equity, selling to a larger company — but in my head, the plan was always: five years from now, we build this thing, we sell it, and we move on. My CEO saw it differently. He was happy to keep running a ten-million-dollar business indefinitely. And there’s nothing wrong with that — it was profitable, it was sustaining, it was a good business. But we were never aligned on where we were heading, and that misalignment created friction at exactly the moments when we needed to be pulling in the same direction.
Have the conversation early. Write it into the plan. What are you building, and what happens to it?
My ten-year-old grandson — for his entire life, every time I have him for the night, he wants a bedtime story. And he wants you to make it up. That’s a big ask. But the thing he absolutely will not forgive is a weak ending. The story can go anywhere, take any turn, but it has to land. It has to have a twist, a resolution, something that makes the whole journey worth it. He’ll tell you if you’ve gotten away with it.
Your business plan is the same. The ending matters. A lifestyle business that generates good income for you, your family, and your employees — that’s a completely legitimate ending. My brother-in-law runs exactly that kind of business. Low drama, consistent cash flow, no particular ambition to change it. He may eventually sell it or pass it to one of his kids, but there’s no reason to change what’s working. That’s a fine ending. Or maybe you’re building to sell — to a private equity firm, to a strategic acquirer, eventually to public markets. Either way: know which story you’re writing before you’re too deep into it. And make sure everyone you’re working with knows it too.
The Money and the Market Fit Together
The finance piece and the market piece don’t live in separate sections of the plan. They’re joined at the hip.
One of the things you have to get right early — and I mean early, before much else matters — is: who is your market, how big is it, and how are you going to price what you’re selling? Once you’ve answered that honestly, you have your revenue picture. Once you have your revenue picture, you can build the cost side. You know what you need to hire, what infrastructure you need, what margin you have to work with.
Those two things — pricing to the market and understanding the size of your opportunity — get overlooked too often. Entrepreneurs fall in love with the idea and skip over the math. The math is what tells you whether the idea can actually become a business.
People Are the Hardest Part
I’ve saved this for last because I want it to land.
You need operating skills to execute a plan — either you have them yourself or you find someone on your team who does. But the thing that will keep you up at night, the thing that will make or break almost any venture, is getting the people right.
Everything else in a business plan is learnable. Market research is learnable. Financial modeling is learnable. Product development has a process. But assembling a group of people who are genuinely aligned — who want the same outcome, who pull in the same direction when things get hard, who don’t fall apart when the plan meets reality and needs to change — that is the hardest problem in business. It’s hard in startups, and it doesn’t get easier when the organization is large.
The plan matters. Tell a good story. Get your five pieces right. Know your ending before you start.
But remember that every single thing in that plan will eventually be executed or undermined by human beings. Get the people right first. The rest you can figure out from there.