The Crossover Checklist

Most people who build something on the side never find out whether it could replace their job. My brother did.

For thirteen years Kip worked at Collins Aerospace. He started as an intern chasing people about overdue training, moved into procurement buying parts for human spaceflight, including the Orion capsule that flew on Artemis I, then into program management, and finally into a site lead role responsible for a business unit of about 200 people.

During those same years, he and a business partner were building MPI-K9, a security company that provides armed and executive protection and working dogs. It began with a website that sold nothing for four years. It now runs about 100 people worldwide and handled security at the Republican National Convention. A few weeks before we recorded, he left Collins to run it full time.

I wanted the part most of these stories skip. Not the leap, but the years before it, and the conditions he set before he would go.

Running both without shortchanging either

The first thing to say is that he did not do it by working more hours at one desk.

His partner, a former canine officer, carried the day-to-day. When a customer needed something at eleven in the morning, the partner or a field operations officer handled it. That left Kip able to give Collins the workday and keep the business to things he could schedule: payroll, reporting, proposals, email. As he put it, most people trying to build their own business are the one person, which is exactly what makes it so hard.

The second thing was the kind of work. His day job was decisions, one after another, all day. The business was different work, and different work rested him in a way that more of the same never would.

Then there were the routines. He was up at 4:30 and in the gym first, because it was the only clear-minded hour of the day: no email, no texts, and the place he did his best thinking before the day started.

And he automated what he could. Instead of billing by the hour, the company bills a standard monthly rate, which makes invoicing something a machine can do. Proposals got the same treatment with AI tools. His summary of it is the honest one: he could not have done both without those tools.

What all of that has in common is that none of it is heroics. It is a situation arranged so that the work does not depend on his best week, which is the same argument I made in Heroic Effort Doesn't Scale. Later he put a name on the goal: buying back his time. Hiring an executive assistant and field operations officers took the administrative load off him, which is what made room for the business to grow.

What finally forced the decision

It was not a bad day at the office. His leadership there was good, and he says so.

It was the nature of the work. Security does not run on your calendar. A client who wants protection wants it in a few hours. A serious conversation means being in Los Angeles tomorrow. He had started spending vacation days traveling for the second business, choosing carefully which meetings he had to attend in person. At some point the arithmetic stopped working: he could be all in on one or all in on the other, and not both.

The Crossover Checklist

Here is what he wanted true before he would leave a paycheck. I asked for criteria rather than a feeling, and this is what came back.

1. The business income has replaced the salary

He did not plan on a pay cut, and did not take one. In 2023 the business made essentially nothing; everything went back in. In 2025 his income was roughly 60/40, weighted to Collins. In 2026 the business was paying about what the salary paid. That was the trigger, not the ambition.

2. No single customer can sink you

The question he asked was direct: if we lose one, two, or three of our largest customers, does this still work, and does a paycheck still arrive? A business whose revenue sits on one contract is a job with extra risk.

3. Cash, not just contracts

Cash is king, and a signed contract is not cash. Early on they covered payroll on credit cards while banks held checks for a week, because the people doing the work were never going to go short. Know how long your customers take to pay and how long the money sits before you can use it.

4. Someone else holds the day-to-day

Everything urgent that arrives while you are at your other job has to reach someone who can act. A partner, an operations lead, an assistant. Without that, the second business can only grow into the hours you are not working, which are the hours you do not have.

5. The household agrees

He is plain that none of it was possible without support at home, through all of it, including a third child arriving in the middle of the busiest stretch. This is not a soft item on the list. It is the one that makes the rest survivable.

6. Ask the question our dad would ask

Our father spent 42 years at one company and thought like an engineer. His question was not "what could this become?" It was: if all of the bad things came true, what would my life look like? Answer that one honestly before you go, not after.

What the buying side taught him

Kip spent years deciding which vendors got work. Now he competes for the contracts. The useful part of that reversal is what it taught him about how the decisions actually get made.

Lowest price does not win. Compliance and quality are thresholds; once a bidder clears them, the buyer is weighing total value. His company competes there by keeping overhead extremely low, which lets them charge less and still deliver better people.

He is also generous about competitors, which surprised me until he explained it. The security industry is small, and the part of it that works with dogs is smaller. "There's enough contracts for everybody," he said. You do good work, you refer what you cannot take, and word travels. That is not sentiment. In a small market, reputation is the distribution channel.

The other thing he carries from the old job is a problem-solving reflex. Asked whether he could source a pair of commercial jets for a client, his answer was that he might not know yet, but he can learn. He is coachable. Then he goes and finds out.

One more thing worth keeping

Late in the conversation we got to the mindset underneath all of it. Plenty of people are in a tight spot they did not cause. A branch falls on the car on the worst possible week.

It might not be your fault, but it is still your problem. Stewardship starts there: not with assigning blame for the situation, but with handling well what is in front of you, including the parts you did not choose.

Square it away

Take one item from the checklist, the one you would rather not look at, and answer it in writing this week. For most people that is the second: if your largest customer left, what is left?

Watch the full conversation with Kip, find him on LinkedIn, and find his company at mpik9.com.