Jon Warner | Becoming an Entrepreneur for the Right Reasons

You’ll probably relate to Jon Warner’s story. Before starting his own businesses (which he was able to sell), becoming a best-selling author, advising startups, and advocating for older adults with his company Silver Moonshots… Jon left the corporate world because he was disillusioned.

It wasn’t all smooth sailing at the beginning. But he wouldn’t trade it. And what he learned over the years – from triumphs and mistakes – has given him a lot of ammunition as he helps other entrepreneurs achieve their dreams.

One of his biggest pieces of advice for prospective first-timers: don’t jump in headfirst, conduct rigorous research into the businesses you’re considering. 

We get into detail on what that looks like and what the best sources of information are, as well as…

  • What questions you should ask to get accurate and actionable data
  • The opportunity in addressing the unmet needs of the over 50 population 
  • A dangerous motivation killer for new entrepreneurs (that could kill your venture)
  • The difference between market research and customer discovery
  • And more

Listen now…

Mentioned in this episode:


Giuseppe Grammatico: Welcome to the Franchise Freedom Podcast. I’m your host Giuseppe Grammatico, your franchise guide, and today we have a very special guest. Today we’re speaking with Jon Warner. Jon is the CEO of Silver Moonshots and works with startup business founders and early-stage company CEO management teams to help them set clear growth-oriented goals and to get the best possible outcomes.

Jon serves on several advisory boards and chairs three of them and speaks regularly about the role of technology and innovation in healthcare and aging 50-plus space. Jon is also the author of his 40th book, if I read that correctly, SLAM to guide entrepreneurs. Jon, welcome to the Franchise Freedom Podcast.

Jon Warner: Great to be here, Giuseppe.

Giuseppe: And we were just talking, you know, 40th book. That’s pretty impressive. Did I read 40th book correctly?

40 Books?!

Jon: Yeah, that was number 40. I, you know, for many years I was writing two a year, would you believe, and I just got into the discipline of writing. I blog a lot. I publish a lot. And I’ve always found it came easy to me. So, the quality may be questionable, but the quantity is certainly there.

Giuseppe: Awesome. That’s great. I just wrote my first one and thought about maybe down the road, looking at a second. So when I read 40 I said wow. So I may hit you up for some advice in the very near future as I start book number two.

Jon: Write every day, Giuseppe. That’s the big advice, right? People get scared at the blank page. Just don’t do it. Just get into the discipline of writing. That’s the big advice.

Giuseppe: Yeah. And actually, and speaking of which, we took, you know, with the podcasts, we started transcribing some episodes and kind of, you know, getting them organized and put together so that was a quick little secret that I learned along the way as well. Got a lockdown, a big chunk of the book down in four or five mini-interviews as we put them. And it’s funny you write the first book, everything is down. And then you realize, Oh, I should have added that or maybe I should have mentioned that. So I already have ideas for what was missing in book one for book number two.

Jon: Yeah. And people crowdsourcing books these days, you know? You get the structure of your book right, you can actually put it out into the world these days, and people will weigh in. And sometimes there’s some quite good ideas it can also write about so there are a lot of good tips and tricks these days into getting a book out there.

Giuseppe: That’s great. I was not aware of that. And I definitely will be having a second conversation before I start that process. So Jon, if you could fill us in, I like to start every episode, we always talk about our audience. Our audience are a lot of, you know, corporate executives, sometimes we call them corporate refugees. People looking to make that leap into entrepreneurship, whether it be a franchise, non franchise business and, you know, looking for advice, what they should be doing, questions they should be asking.

And we also have our audience, our current franchisees, current business owners that have made that leap and they are looking kind of for the next investment, next vehicle, ways to diversify not only their investments, but they’re also looking at a potential exit strategy. So that is kind of the audience. So if you can fill the audience a little bit on your background, how did you get started in your current business, and what does the journey look like?

Jon’s Entrepreneurial Journey

Jon: Sure, happy to do that. So I was one of those corporate refugees, if I go back far enough. I worked for Air Products and Chemicals, a pretty major corporation up in Pennsylvania. I worked for Exxon Mobil many years and I was climbing the corporate ladder but got pretty disillusioned in doing that. So, at the tender age of 35, I decided I had enough of corporate life and wanted to go on my own. I always had some entrepreneurial ambitions.

And I started a consulting business early on as a small business, and just literally tried to take that to marketplace, learn from my mistakes in doing it. But realized I needed to kind of retool, relearn what was needed because working in a small business is very different. I was super naive about what it took to succeed. You have to wear many hats, you have to take on things like the sales function and really understand the finances of the business, etc.

So that was a learning curve. It ultimately succeeded. I grew that business to about 30 people before selling it. And then I got the bug for being in small business. So I went on to have two more startups of my own that I founded and sold. And then from there went on to kind of parlay my experience because I’ve had three startup organizations, it’s where my writing career started.

So I started both writing and teaching entrepreneurship in general to those very people who wanted to come in the space, into the space. And try and give them some of the toolkits that they needed to succeed and maybe not experience the mistakes that I had. So that was kind of the journey. These days, I do a lot of both advisory to early-stage companies just trying to guide them. And that’s particularly when they need to raise capital if they’re in a full startup. But equally, I spend time with individuals who aren’t ready for that full step into a startup of their own.

They might just be looking to license an idea and just go through the ideation process and they still need to engage in good product thinking, good customer discovery, thinking about who the markets might be and the targets. So there’s a lot of entrepreneurial thinking in that. And the same goes for franchising. I don’t think anyone should just jump into franchising, you know, with both feet. I think there’s some research to be done in preparing for that step. So, I spend most of my time these days trying to help people think through that journey.

Giuseppe: Right. Yeah. And I mean, obviously, definitely have a passion for entrepreneurship both what you just said and prior to the show today. So before we get into the kind of the business, how you help current businesses and startups and things like that, if we take a step back, so prior to the show, we had talked, we had a little conversation about career transition.

And there’s a lot going on in the world, right? With the pandemic, with people, either they have, you know, always thought about maybe starting some type of business and it’s kind of been on the back of their mind. Other people have been kind of forced into trying to figure out what’s next as they have been furloughed and maybe have been downsized, you know, from their jobs. So what advice, you know, you’ve been doing this for a while.

What advice would you give someone going through a career transition trying to figure out if business ownership is the right fit? Because, you know, quite frankly, you own multiple businesses, I have as well. It’s not easy, right? Whether it’s a franchise, whether you’re going the license route, whether it’s neither, you know, just a startup on your own. This is not easy. It requires a lot of work. Now, what advice would you give, a couple pieces of advice for that person looking to make the transition?

Advice for Those Looking to be Their Own Boss

Jon: Sure. So the biggest advice, I think, and the one you want to dive into the most is really doing as much research as you possibly can about the journey ahead. I think as you alluded to, I think sometimes people get into small business by accident and it’s the accident of maybe being furloughed, but we know more often than not, you know, perhaps they collect a redundancy package or they suddenly find themselves out of a job and think, well, maybe I can make more money or maybe I can, you know, life would be easier if I were in charge of my own destiny.

And there’s nothing wrong with that as a thought. But I think you’ve got to really think that through. So how do you do that? You’ve just got to pay attention to others who’ve done it. So I think it’s great to actually talk to small business owners, franchise owners, people who licensed products and even entrepreneurs. These days, you can read about it. You can web search, you can listen to podcasts such as yours and many others that are out there these days. We know the podcast industry has exploded.

There is some absolutely fabulous advice available, you know, these days in many quarters. You can watch people talk about particular topics. So for me, I think the foundation is almost going back to school. It’s getting back into a learning mindset that says I shouldn’t naively jump into this and think I can be successful on day one. I need to kind of train my mind and, you know, get filled up, if you like with as much good knowledge as I can possibly muster before I make that choice to go into something.

So that would be the first thing. Go deep dive on the learning side payment, pay attention, you know, take as much time as you need. Certainly weeks if not months. And then secondly, I think you’ve got to make sure you’re leaping in the right direction. You know, it’s fairly old advice, but it’s good advice. People should sort of do things that they’re passionate about and they care about. So you’ve got to think about what would make you happy when you’ve done it.

There’s nothing worse than jumping into a business, it doesn’t matter what it is, and you suddenly find six months later, you know, I really don’t care about this product, these customers. This is not my passion. You’ll find your motivation just dissipates super quickly and you’ll find yourself in the wrong place. So I think you’ve got to research what would I enjoy doing? And again, prepare for that step. So I think those are the two things. A lot of research ahead of time. And then make sure you’ve kind of aligned your values and your passions with what it is you want to try and do.

Giuseppe: Right. I absolutely agree. And, you know, have that vision, you know, why, you know, kind of talking about, you know, interest and things like that, but why are we doing this in the first place. Do all the homework, as you had mentioned. And part of that homework too, is I think, and correct me if I’m wrong, but it seems to me and I am guilty of this as well. We go online and we just start doing research and reading articles and it’s, you have, it’s knowledge overload.

And I always jokingly say knowledge is not power. It’s how you apply that knowledge, right? So we’re all filled with knowledge. We all know the workouts to do but are we doing the workout? You know, you kind of need that coach to assist you. So, you know, really just, in my opinion, you know, some of the advice, I wish it was advice given to me.

I actually kind of figured this out the hard way and it took me a lot of time but I got off the internet and just, you know, in my franchise journey when I was looking at franchising, I just started picking up the phone or visiting franchisees at their stores and just saying, hey, looking at opening up that franchise. What are your thoughts? Would you, you know, the million-dollar question, would you knowing what you know now, would you do it all over again?

And having conversations with people, I think people have seemed to shy away from that, Jon. It seems to me they just like, yeah, I’ll do some research online. I’ll read a brochure or I’ll look at a webinar, but just really having that dialogue one on one sometimes, especially in person, sometimes goes a long way. You get some honest answers. Maybe someone will shy away if you’re asking for advice in a group but if it’s one on one with an owner, you’ll definitely get, you know, some honest feedback, I think. Some really great, honest feedback.

Customer Discovery

Jon: I agree and let’s talk about it because I think it’s the way to de-risk what you’re doing. And I couldn’t agree more. I think face to face conversation is ideal and even in COVID when they can’t be face to face, it’s so easy to get on Zoom now and meet someone. And I don’t think people are too resistant. Most people like talking about themselves.

So if you bring someone out and say, Hey, can you tell me about your business and can tell what you like and you don’t like, I think people are pretty disclosing. And this is all in service of something that the Lean Startup Movement called customer discovery. We didn’t even call it customer discovery 10 years ago. And it’s not the same as market research. Market research is a formal affair. You know, you send out the Mailchimp questionnaire and you ask people a bunch of questions with drop-down menus.

That’s fine. But that’s usually not the product level, you know, you’re picking whether it’s, you know, blue or yellow. Customer discovery is getting face to face to people and trying to get into their shoes, understand how they kind of live their lives, attend their games, and all the things that you need to know ahead of time. I think that is the beginning of all startup journeys. It’s the rigor of getting deeply into customer discovery. And it’s not you pushing an agenda on someone. It’s not thinking I’ve got an idea. Can I kind of pre-sell it to you? I think I’d be a really good startup person doing this. You’re really in listening mode and that’s the big difference.

You’re there making sure that you’re getting good information, even if it invalidates what you’re thinking. So if you’re thinking wow, of this franchise or this business would be really great and they, you know, the feedback you get is well, no, it wouldn’t. I think it’s saturated. I think there’s too many competitors here. I think the prices are wrong. That’s a great way of finding out that this may not be for you and you should switch or pivot, as people like to say these days, into something else. So I think it’s crucial to do as much customer discovery as you can as early as you can.

Giuseppe: Yes, I agree. We call it validation calls on the franchising side and that is crucial, you know? Obviously, franchise development person will give you all the answers you need and all the information but you want to hear it directly from the people doing the work and running the business day in day out. And one additional, and just to kind of one last piece of advice that I learned the hard way with validation, I know specifically when you’re even looking at a, you know, at a franchise business, don’t just call people in your backyard. That’s the mistake I made.

Call people, I’m in New Jersey, call people, you know, Jon, by you, your office is in California, you know, Florida, you name it. Call them all over him. And people say why, and I found this out and without naming names and without, you know, embarrassing anyone or any specific company, the original franchise I had looked at, I thought was a perfect fit. And the franchise owners I spoke with did not give me the best feedback. And for years, I couldn’t figure it out. You know, they didn’t give me the best feedback. I just, it didn’t leave a, it left a bad taste in my mouth.

So I ended up doing other things and was happy. Did well and, you know, not looking back. But as far as the advice I give to future franchise owners, I found that the advice that was given to me was actually biased and false because, you know, I was looking at an open territory. And by developing in that open territory, the existing franchisees felt I was going to infringe on their business because that open territory, which was a few counties here in New Jersey, were wide open.

And since there was not anyone developing, they were able to kind of go in and pick up an account here and there. So I found this out years and years afterwards. And by the way, I’m not saying, you know, this will happen or this is what goes on in franchising. It just was a specific instance that happened to me. I wish I was prepared for that. I was not so I learned that the hard way. So it’s my free advice that I kind of give to everyone. So

Jon: I agree with you entirely. I think you cast a broad net, you make sure you’re not too parochial, that you get corroborative kind of input. I also think there’s one other little wrinkle that I can add if I can which is be careful that you’re not leading the witness. I think a lot of people engage in what you call validation, I call customer discovery with a kind of a mindset that says, I’m here to prove that I’m right. And the problem with that if you have that conversation without mindset, you’re really getting people to say yes to things they might not say yes to if you ask them a different way.

So we know that leading a witness is something you do in the court. You know, you say, you know, were you there on the night of Tuesday, the 16th? And you’re gonna get a yes or no answer out of that, or you’re gonna, you know, you’re trying to go and push them in a certain direction. You really want to go and ask open questions. So you’re more about an investigator. You know, you’re just someone who’s there like a detective in a story such as, let’s say, you’re talking to a franchise owner, you really want to go and say to them, tell me about your business.

Tell me what keeps you up at night. Tell me what’s good. Tell me what’s bad. Tell me what you would have done differently if you were to tell your younger self five years ago some good advice. Those are the questions that are likely to reveal more about the good, the bad and the indifferent. Then go in there saying, you know, how great is it to be the franchise manager of a Dunkin Donuts? I mean, you know, in the end, you’ve just led them down a path and then what are you getting out of that? So I think you got to be careful how you think about this.

Giuseppe: Right Absolutely right. Yeah. Don’t set them up to get the answers you want. Absolutely. That’s just, that’s sabotage there. And at that point, there’s no even additional point in even doing the meeting or the interview.

Jon: I actually coach people in asking questions. It’s amazing how much they do set people up for the answer that they want. And they show their research and pretend that they got 10 people saying this is great. They’re just asking the questions in the wrong way.

Giuseppe: Yeah. And by the way, and one last thing on that with the question that I said the million-dollar question in knowing what you know, now, would you do this all over again? That is, you know, that’s not an open-ended question unless they elaborate. If they say no, and you’re like, Oh, that’s not good. Well, find out. If they say no, you know, for example, going back to Dunkin Donuts, I wouldn’t do it all over again. Why?

Well, because, you know, maybe it’s their specific market or their role, which I hear is not matching with what they wanted to do. You know, they envision just having this grand business and just kind of overseeing it. And now they’re a manager and they’re dealing with HR all day long. Find out because it may just be a specific mismatch for that specific owner. So always have them elaborate and ask why, why, I always say ask, why five times to get really deep in your answer.

Jon: Just like a little kid, right? When mom tells you, you can’t go out to play, you have to keep asking that why question. And so, you know, maybe people are not that comfortable doing it. I think the other great question is tell me more. So if someone says something, you don’t have to go and tee up the next question that’s on your pad. You can just say can you tell me more about that. People will disclose. It’s amazing if you practice this. And practice on your family, practice on people you know and you’ll find it’s just, it reveals so much great information.

Giuseppe: Right. Yeah, absolutely. I definitely agree there. Yeah. And great conversation. You know, there’s definitely, so kind of the sum up different, definitely want to do some thorough investigation in any business, figure out why you want to do it as Jon and I were speaking about. There’s different paths. No path is better than the other. It’s the path that definitely matches what you’re looking for.

So, Jon, talk to us a little bit about, you know, startups. Companies that either are, I guess, you know, starting up their businesses or existing businesses. How do you help businesses? You know, what specifically do you do? You know, do you only work with certain size businesses, types of businesses? Can you elaborate a little bit more on that?

What Types of Businesses Jon Works With and How He Helps Them

Jon: Well, we all get a little bit typecast as we get older, and that’s true of me as well. So I teach entrepreneurship. So I see a lot of would-be entrepreneurs from many sectors. But I have to say the vast majority these days are in the healthcare sector. So it’s people that are trying to serve that sector in a multitude of different ways because it’s a very big sector.

Healthcare is not really an industry. It’s about 125 separate sub-industries. It’s 20% of our GDP. So it’s a giant sector. And then within that, I actually like startups that are trying to solve the problems in the older adult space, which for me is people who are over the age of 50. And that’s because they’ve got a ton of unmet needs.

There’s a lot of people in the 50-plus marketplace that are looking for products and services that are just not there yet. So the opportunities to bring those products into being are massive. So I, that’s where I’d most like to help in terms of the mix. In terms of how, I am going to appropriate your work, I think there’s two things I mainly do. One is helping with a validation journey. You know, do you have a path that’s clear, that’s solving for a real need in the marketplace.

Even If you’re evaluating something, you know, does this particular franchise in this location at this time look like a good idea? You know, or as opposed to a completely brand new startup. That’s a journey. You have to dig into that do the data, do that customer discovery we talked about. Have a value proposition that, you know, is really compelling and is different to everybody else out there that’s going to win ultimately. And then if and only if they can get that validation to the right place, I help them with the execution journey because that journey is the hard work journey.

It’s the sweat journey where they have to really understand how to execute on the plan, which usually means good leadership, putting a good team together, making sure finances are in place, and then well controlled when they are, good marketing systems. So execution is a pathway all by itself but it needs to sit on the bedrock of a really well-validated idea and a clear value proposition. So that’s where I help the most trying to help those organizations, whoever that may be, do those two things.

Giuseppe: Right. That’s great. You know, with your business as you’re working with, you know, different types of businesses, what’s exciting? I mean, there’s a lot going on in the world, but what’s exciting, what’s new, what, anything you want to tell the audience about?

Jon: Yeah. So let me give you some context. So what I do in Silver Moonshots that you mentioned earlier, is we run this nonprofit accelerator. I run it as a nonprofit because I want to increase the deal flow of people who are coming into entrepreneurship and coming up with new ideas. So we bring six companies into the cohort every quarter. So every three months, we have six new companies. We run a little six-week curriculum.

And they do a whole bunch of customer discovery in that six-week period. We’ve been doing this for nearly two years now. It’s a lot of fun because they’re out there testing their ideas and talking to customers and really validating what they’re doing. I get super excited because I, as I mentioned, a lot of these companies are aiming at the older adult marketplace so they’re talking to people about a range of ideas.

And they might be really top of mind stuff that we’re all concerned about now. So it’s people protecting themselves with PP, it might be around COVID in general now to be safe. It might be about markets like the cannabis market, which in California has completely exploded since we deregulated that marketplace. So it might be CBD, for example, for older adults, and how can we supply products to market in a different way that are more fit for purpose, etc, etc.

So I get excited with a lot of startups that are trying to bring new thinking to bear. And it invigorates me. So I see all sorts of wonderful opportunities, all of which are enabled by amazing technology now. Just the advances we’ve seen in terms of digital platforms. And what we can do on the back of a smartphone now, or artificial intelligence and algorithms that can get chatbots to market, for example, just give us so many opportunities that weren’t there even 10 or 15 years ago. So it’s a very exciting time.

Giuseppe: Yeah, that’s great. Wow, that’s very interesting. And I was checking that out on the website. Jon, if someone wanted to reach out, so they’re not certain what direction to move in, needs some advice, you want to maybe see if they’re a good fit, good candidate to work with, what’s the best way they can reach out to you?

Jon: Yeah, there’s two ways. If your focus is on the older adult marketplace in general, then go to the website. There’s a contact form there and there’s actually some free materials on there to go and look what others have done, previous cohorts, we’ve run, etc. And that will come to me. I see all of that traffic as it relates to that website. And then in terms of, you know, the validation framework stuff that I do entrepreneurially, I have a website dedicated to my last book, it’s called

That website also has a contact page on it. And that has a ton of free resources. There’s some video resources on it. Actually, the validation map is right there and resources within that website, that’s probably worth people looking at. You can reach me through that. And then of course, to all the usual social media links. I’m on LinkedIn. I’m Jon C Warner on LinkedIn. And Jon has got no H. It’s just JON. But you can find me and reach out, message me. I’m more than happy to talk to people.

Giuseppe: Sounds great. Anything else that you’d want to, and by the way, that’s all going to be in the show notes. Anything else that we didn’t cover today? I feel like we could be talking here for a few hours.

Jon: Good conversation. And, you know, the one thing I’d leave your listeners with just as a thought is I think entrepreneurs are heroes. And when I say entrepreneurs, I mean anybody who’s ideating, just coming up with new ideas, new thinking, individuals that take on small businesses and franchise and people who start businesses from scratch.

They’re all heroes. We need more of them. You know, do your research, as I said, because this is not an easy journey. So do your research, do it carefully, do your customer discovery. But take the leap if you think that you’re getting good feedback. It’s wonderfully rewarding. You do take control of your own life. So if it is on that bedrock of good research, it can be a very rewarding journey. So but they’re brave people who do it and I applaud all of them.

Giuseppe: Yeah. It’s not easy but from experience, and I’m sure we both agree as we discussed earlier, definitely worth it if it’s, you know, for me it was all about the time freedom. It wasn’t, you know, money is nice, but just being able to spend time with family and not be on rope.

Jon: Being your own boss and choosing how you spend your time. I think those things are super rewarding.

Giuseppe: Right. Do your homework. I know. It sounds scary, dangerous, risky, but I feel doing your homework, working with someone like Jon or myself getting a little bit of more of insight, making sure that the questions are getting answered for you.

And I think that information and applying it definitely de-risks the whole project. You know, you start to get a little bit more educated and informed on the business and you’re like, Okay, well, for example, I know I need to bring in X amount of customers every month to break even. I can easily do that. So I thought it was a much greater number. So I think once you break it down a little bit, it definitely helps with the overwhelm and what the implied risks

Jon: Yeah, and it’s a good way to think about it. I always say if you’re b2c, you have to ask yourself the question, what would it take to get my first hundred customers? And can I do that? And if you’re b2b, what would it take to get my first 10 customers. Not a bad rule of thumb to think of average as part of your research.

Giuseppe: Right. Before that, once you don’t have a plan, you’re just looking at numbers. It gets to just be, you know, intimidating to be quite honest. And once you have a plan and break it down you can make that educated decision. Jon, it was great to have you on the show. We include, as I mentioned, everything, so all your contact websites, everything will be on the show notes and wanted to thank you again for being on the show.

Jon: Great stuff, Giuseppe. it’s been good talking.