Since I began Trajectify, I’ve had the opportunity to coach a number of family-owned businesses, from intergenerational companies to husband-and-wife teams. In some ways, they face the same challenges as any other business. They have to figure out how to maximize their cash flow, hire the right people, and scale their business.
Family-owned businesses also have their own particular set of challenges.
Read MoreStartups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
Founders tend to think about a major transition as a singular event. You prepare, announce, close, and now you're a different company. In my experience, the company starts changing well before any of that happens. I've been through this several times now, and the details were different every time. The weirdness was pretty consistent.
Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Ask a room of leaders why they set goals and most will say accountability. That answer creates the problem. Goals exist for alignment. The company needs to reach a number, so this group does this, that group does that, and together the math works. Everyone is pointed in the same direction. Focus comes second. A good goal tells you what to say no to.
The instinct to build a team that moved in the same direction, at the same pace, with the same set of perspectives is limiting. Consistency is created at the expense of range. The goal isn't alignment of strengths. It's coverage. The most dangerous teams I've seen weren't the ones with conflict. hey were the ones with none. Where every conversation ends in agreement. Where nothing gets surfaced. Where the people who see things differently may have learned to stop saying so.
The same restlessness that makes it hard to stay on plan is what made them start the company in the first place. The wandering mind, the refusal to be satisfied with what already exists, the ability to see something before it exists: that's not a disorder. That's the source.
If you're building a company, knowing your role isn't optional. The visionary needs someone who will build what they see without getting in the way of the seeing. The integrator needs someone who will point at the moon and mean it and keep pointing at the same moon long enough for the bridge to get built. The mistake I see most often: trying to be both or hiring someone who mirrors you when you need someone who complements you.
The fear of success doesn't usually announce itself as fear. It sounds like planning. It sounds like due diligence. It sounds like being responsible.
What it actually is: A limiting belief. It’s spending today's energy on problems you'll only face if you win
TEAM | INTERIM EXECS | COACHING | PEER ADVISORY | SERVICES | RESOURCES | CAREERS | CONTACT
Copyright 2026, Trajectify LLC. All Rights Reserved.
Most founders and executives I work with are uncomfortable talking about how they look. It feels shallow. Not the point. I get it. They started their companies because of a vision, not an ego. By the time they're working with an advisor, they're wrestling with real problems: who belongs in which seats, how to build accountability, how to run a leadership meeting. Thinking about personal image can feel self-indulgent by comparison.