Mike speaks at the historic Trenton Computer Festival.
8 Lessons From 8 Startups
Mike will share stories from his time at 8 pioneering startups that result in 8 lessons to educate and entertain technologists and entrepreneurs. These lessons explore the intersection of technology, economy, people and leadership
Startups 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.
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
Right people, right seats doesn't mean everyone eventually moves into a leadership role. It means finding the seat where each person does their best work and building a structure that makes those seats worth staying in. Create a path for people who want to grow as individual contributors. Create a separate path for people who want to lead. Reward both. Respect both. Pay both.
Don't prevent scraped knees; prevent bus crashes. A scraped knee hurts. You might carry the scar for years. That's the point. The pain is proportional to the lesson. A bus crash can lead to catastrophic loss. The project. The company. The relationship. Something that can't be recovered. The leader's job isn't to eliminate mistakes. It's to know the difference between those two things.
The leader's job isn't to have the answer. It's to create conditions where the best answer can emerge. That means encouraging disagreement without punishment. Creating opportunities for information to move across functions. Making it safe for people to challenge assumptions, including your own. The highest-performing teams in these simulations don't succeed because they have the smartest leader. They succeed because nobody in the room is waiting for one person to have all the answers.
The leaders who are consistently good at managing up and across understand something most people miss: influence gets built long before it’s needed. Not through charisma. Not through politics. Through small, deliberate actions repeated consistently over time. Investments. Relationships are like a bank account. You have to make deposits before you can make withdrawals. Most people get this backwards.
The leaders who build something lasting lead differently. They retain great people, create cultures that outlast them, and build organizations that can function without them. They share power. They create it in others. When a team operates out of fear of authority, they do the minimum required to avoid consequences.
TEAM | INTERIM EXECS | COACHING | PEER ADVISORY | SERVICES | RESOURCES | CAREERS | CONTACT
Copyright 2026, Trajectify LLC. All Rights Reserved.
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.