Help! I Want to Switch Gears and Found a Startup

Dear Mike,?

I've spent the better part of my career helping other people with their companies. What I really want to do next is start my own business, but I’ve never done anything like that before. My expertise lies in stepping into Series B SaaS- model startups that have already found their footing – usually ones with a solid user base and significant revenue, to scale their company rather than build it from scratch.??

In these roles, I've worked with dynamic teams, pushed the boundaries of workplace communication, and seen firsthand how technology can transform business operations. We're talking about companies that were out of infancy but hadn't quite reached peak maturity either. It's been personally and financially rewarding, and, frankly, comfortable.?

Lately, I find myself at an inflection point in my career. I'm contemplating breaking out on my own, which is something I've always envisioned but never acted upon. I have an idea, one that I believe satisfies a unique gap in the market: an internal communication tool, but with a twist. It's designed for enterprises, integrating AI to weave proprietary knowledge bases into the fabric of everyday interactions. It's ambitious, maybe even a bit presumptuous, especially in a space that's as crowded as a Tokyo subway car at rush hour.?

The problem I’m facing is that my resume is noticeably void of "From Scratch" experiences. I've always parachuted into established zones, where the basic frameworks were already constructed, and the task was more about scaling than creating. I've never had to sketch a business model on a blank slate, chase after seed funding, or navigate whimsical currents of seeing my own idea through to the end.???

There's a voice in my head that I can’t seem to shut down: "Are you really cut out for this? Steering a ship in calm, open water isn’t the same thing as getting it out of harbor, let alone building that ship from nothing." And I am hardly the only self-identified seafarer out there – I know I am splashing into the most saturated market of all time.???

But I still want this, so I could use some introductory guidance. How can I get started on getting started? What do I need to learn to build a solid foundation, ensure the right product-market fit, and attract initial funding? Are there lessons from my late-stage experiences that could be invaluable in this new phase???

Yours sincerely,?

A Hopeful (but somewhat daunted) Aspiring Founder?

Dear Hopeful and Daunted,?

I encourage everyone to pursue their ideas, pursue their dreams, pursue whatever you want – but not before you school yourself on exactly what you’re signing up for before you do. The world of startups represents a major shift from what you’re used to, and there are some critical questions you need to ask before making any irrevocable decisions.?

First, do you have any family gold bars buried out in the desert? What about a substantial nest egg that you’re willing to burn through? Can you handle a substantial period of little to no income? Because building the type of company that you’re talking about is not a cheap endeavor. (In fact, you’d be hard pressed to find any company that is a “cheap endeavor” to build.) I can’t think of any founders, particularly in the tech space, who could build a platform, launch it, acquire customers, and generate revenue without a securing substantial external investments. Thinking that through – how you would go about it and whether that’s feasible for you – needs to be your immediate first step. If you can’t sail over that hurdle, then nothing is going to gel in practical terms.??

Second, are you single? If not, are you ready to suddenly become single? I’m not trying to rain on your parade; it's entirely possible that your partner is heroically supportive, willing to stick by you through every trial and tribulation. Even if that's the case, are you sure your relationship can weather the extreme stress that this will put on your relationship? Do you have the emotional stability to handle the ups and downs of starting a company, and does your family? Starting a business usually means giving up all your free time, energy, and emotional resources. It’s a bit like throwing your life into a pressure cooker – great for making decisions under heat, not so great for peaceful evenings at home.?

Starting a business usually means giving up all your free time, energy, and emotional resources

Third, do you have a plan beyond the product itself? Given that this is your first foray into building a company from scratch, I advise you to spend some time thinking about your network. Do you have the connections to build a venture like this from the ground up? If so, are any of them potential customers? Investors? Publicity opportunities? How will you convince them that your idea has legs, legs that can run faster than the other ideas on, what you’ve termed, “this crowded subway car?”???

As much as I hate to say it, the startup sphere consists mostly of aggravation and failure. Sure, we hear about the successes, but the truth is that those are in one in a thousand. (The successes certainly make for better stories.) Pursuing this isn’t so much chasing a dream as gambling against enormous odds, and it’s worth thinking about whether it’s the risk that makes this whole project so exciting. There’s a great quote? that says it better than I can: “I figure you have the same chance of winning the lottery, whether you play or not or not.” I realize that it’s much more popular to insist that you miss 100% of the shots you don’t take or that fortune favors the brave, but that’s not the reality in the startup world, and you’re not doing yourself any favors by imagining otherwise.??

It’s much more popular to insist that you miss 100% of the shots you don’t take ... but that’s not the reality in the startup world

Have you considered bringing your idea to an existing company? This is often a better and less onerous route. It mitigates some financial risk and gives you a structure within which to work. Though it might not be as glamorous as heading out into the wilderness on your own, it could be a smarter play. I guess it depends on whether you’re trying to evolve into a superhero or actually get a business going. Personal development is admirable, but the stakes here are much higher than they need to be – and not just for you.??

So, my advice? Probably don’t do this. But if you’re going to, use every contact you have – you never know who might be interested in investing in or advising on your project? Leverage your experience. From your time with Series B startups, you understand what drives growth and scalability. Use this to critically assess how your product will stand out and meet an unfulfilled need in the market.?

Daunted but hopeful is probably the best thing you could be right now. Keep your eyes open and always hedge your bets.?

If you are going to take this journey, then I hope the road rises up to meet you. But remember, fortune favors the prepared more than the merely bold.??

Mike?

In today's business climate, most of us feel unsure at least a few times a week. If you have a question about a difficult workplace scenario, my inbox is always open. Message me here on LinkedIn or leave your questions for me anonymously . After 22 years as a serial fintech entrepreneur, I've averted my share of disasters. Let me help you outsmart yours.