At Bootstrappers Breakfast, we often hear a wide range of marketing challenges that entrepreneurs and young businesses are looking to solve– such as lead generation, developing a strong online presence, time management, focus. This time we broke down the content strategy puzzle.
Read MoreThe NYC Bootstrappers Breakfast is back… with new mentors to help facilitate serious conversations about starting and growing a business. Thanks to our friend Alex Portera, Co-Founder of Nowhere Men Media, here are a few quick and valuable points from the inaugural NYC Bootstrappers Breakfast comeback.
Read MoreMost of us take care of things that are important to us on a regular basis – maintaining our car, going to the dentist for a checkup, and updating software on our computer. But do we take a step back and invest the energy to look at our business model to see if everything is working the way we’d like it to? When you take time to review your business model, you may be surprised by the value you discover by making some tweaks – or perhaps even reinventing what you’re doing and how you’re doing it.
Read MoreI was planning to be entertained, which I was, but surprised at how many notes I took. Speakers like Ed Mylett, Andy Frisella, Hank Norman, Tim Storey, Micheal Burt, and Lewis Howes were surprisingly moving and informational - hence motivational. I also got to meet Silicon Valley mogul Naveen Jain. We also had speakers for sales training and marketing education, one who sold $3M in product right after his presentation. Who needed training when you could watch the masters sell right in front of you?
Read MoreI was at a crossroads. Trajectify had grown to keeping me busy nearly full-time. I was organizing the Philly New Technology Meetup (PNTM). And I had my tech startup, IntroNet. For Trajectify, I was working with private clients, small groups, and doing a lot of speaking and business development. For PNTM, we were growing without bounds (nearly 3,000 members in less than two years), gaining sponsors, doingbigger events. merged with Mobile Monday Mid-Atlantic. As for IntroNet, things got very exciting as we saw a pivot from our introductions systems to doing something bigger and bolder with groups sharing their collective connections, expertise and information. I raised $1M for IntroNet.
Read MoreI do think it’s important to be able to feel passion. I have a lot in my life for which I am passionate. I just don’t let passion run my business. That’s a revelation that has come to me over the past couple of years, mostly as I’ve been building Trajectify and able to look at many companies from the outside-in and work with dozens of entrepreneurs. Two years ago, I was likely quoted as saying that passion is the first thing I look at when evaluating an entrepreneur’s business. I was wrong. The way to grow a business is through being practical, measurable, and grounded, not by being “barely controllable.”
Read MoreI just got back from Suzanne Evans' Be The Change Event - something different that any event I’ve ever attended - with lots of stories and lessons learned, some of which I’d like to share. The punchline - which you’ll get if you read further - is that you need to keep an open mind and look for learning in every situation. While I’ll likely never be a member of Suzanne’s “tribe” or attend the event again, what she taught and how she executed gave me some invaluable lessons, one’s I’ve already started to use, and I think made me a little less judgmental.
Read MoreWe spend a lot of time in the office - working with our team, on our projects, with our money (investments, revenues). We see our business through the eyes of those who know us well - employees, investors, family. It’s a very narrow perspective that we get when we only interact a typically homogeneous and friendly population. Every week, I drag entrepreneurs out of the office nearly kicking and screaming - they say they have too much work to do! - in order to me to help them view their business by talking with customers, competitors, partners and their market. Here are three stories to show how some of my clients and I did millions of dollars in deals by following an outside in approach.
Read MoreOne of the first things that I do with each new engagement is to work on goals - for the company and the entrepreneur/leader. It might seem basic, and many have done it before, but my experience is that few entrepreneurs and companies have current goals or have been able to do them well. We don't move forward without goals - it is difficult to grow a business in the absence of them.
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.
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
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.
TEAM | INTERIM EXECS | COACHING | PEER ADVISORY | SERVICES | RESOURCES | CAREERS | CONTACT
Copyright 2026, Trajectify LLC. All Rights Reserved.
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?