To Moonshot, Or Not To Moonshot, Your Business?


If you’re a regular reader of this column, you know that I’m all about transforming a smart, moneymaking business into a moonshot. In fact, I lead a weeklong workshop at Oxford University called Moonshots & Moneymakers for entrepreneurs looking to do just that.

Quick review: A ​smart business (aka Moneymaker) encompasses four important elements:

  1. Self-funding with minimal debt or outside equity investment
  2. A focus on sustainable growth, ensuring long-term success rather than short-term gains
  3. A unique competitive differentiator in the market
  4. Scalable systems and processes to drive efficiency and productivity

A Moonshot distills the essence of a Moneymaker for a much larger total addressable market. The path from Moneymaker to Moonshot begins with seeing an opportunity to apply technology (element #4 above) to make a profitable business into a scalable business worth many multiples of revenue.

Take the example of Jere Simpson, founder of IT security firm KITEWIRE. His business started out as a government contractor building security platforms for the likes of the FBI, and quickly became a moneymaker. Soon enough, Simpson had something extraordinary in his hands: a software security platform tested and approved by the FBI that he, not his customer, owned. Why does that matter? Because software—especially today’s software-as-a-service (SaaS)—is expensive to develop, but infinitely inexpensive to scale. Long story short, once KITEWIRE created its SaaS product for individuals and businesses around the world, it became very valuable. How valuable? Just three years after launch, Simpson sold it in 2021 for $1 billion.

That said, though, there are a lot of reasons for building a company, and they don’t all involve working toward a billion-dollar payday (and all the time, stress, and risk that entails). Instead, you may want independence, time for your family, a reliable source of income, or a business you can pass along to your children or employees. It is really about defining what success looks like for you.

Three Entrepreneurs, Three Definitions of Success

I recently spoke with three entrepreneurs who run smart businesses to see where they placed themselves on the Moneymaker-to-Moonshot continuum. Here’s what they told me:

“For us, it’s about staying true to who we are,” says Donna LaVoie, founder and CEO of LaVoie Health Science, an integrated strategic communications firm. “We have trademarked methodologies that we deploy, and we can continue to develop those methodologies and train our staff on them.” LaVoie sees plenty of growth opportunities along her current path, but that doesn’t mean she’s averse to innovative pivots. Quite the contrary. “We’ll continue to combine our knowledge with the use of other tools,” she says, noting, “I just stepped out of a conversation on how we might use [artificial intelligence] for [public relations], and how we can guide our clients through some of that from a risk mitigation standpoint.”


“It will make us more valuable in the future and more attractive to a wider variety of potential strategic partners.”


Andrea Fryrear, co-founder and CEO of marketing consulting and training company AgileSherpas, is currently contemplating a potential Moonshot. “The interesting next phase is more of a productized blend,” she says. “There are lots of exciting ways now for people to access us when we’re not there with them,” such as self-directed online learning. “It increases our efficiency,” she continues. “One person can serve more clients, and it can also broaden our reach so folks who might never be able to retain us at a private engagement level could still access helpful content. That’s really the exciting place for me. It will make us more valuable in the future and more attractive to a wider variety of potential strategic partners.”

Stacia Nelson, founder and CEO of Pivot Strategies, a communications agency specializing in internal communications, organizational change management, and environmental, social and governance reporting, has a somewhat different take, but no less ambitious. “For us, market domination is the goal,” she says matter-of-factly, “whether that’s continuing to grow organically and/or looking for companies that we could acquire that would help us to grow more quickly. We are also looking at creating a product. However, I would say one of the things I love, and I really believe as an entrepreneur, is that you’ve got to stay close to the things that make you feel alive.”

In the end, they all agree that one’s impact on the world is the key to satisfaction, whatever form that takes. Nelson summarizes with a quote from the 18th century theologian John Wesley: “Do all the good you can, by all the means you can, in all the ways you can, in all the places you can, at all the times you can, to all the people you can, as long as ever you can.”

How big are your entrepreneurial dreams? Are you looking to change the world all at once or one customer at a time? Share your thoughts in the comments!

In the meantime, sign up for our free How I Did It monthly video series to hear my complete conversation with Donna LaVoie, Andrea Fryrear, and Stacia Nelson, along with interviews with other fascinating entrepreneurs.



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