EP 007 | Growth Under Pressure: From infantry veteran to Dragons’ Den to exit: A founder's unconventional journey, with Jon Caldwell

Jon Caldwell built a brand from zero to a profitable exit after serving in the infantry in Afghanistan. When a 4-month Dragons Den delay created a working capital challenge, he self-funded through a software sales role, hitting 120% of quota while scaling his company. Now the founder of 3Victor, he shares the unconventional path that taught him why disciplined execution beats perfect strategy.

‍

🌟 Highlights

• Dragons Den sweep: All 5 Dragons made offers
• The 4x inventory bet: Calculated risk that returned 3-4x wholesale growth
• Exit timing: "Either grow aggressively or get out" - knowing when to sell
• B2B growth playbook: Outbound → Content → Paid (in that exact order)
• Military to startups: discipline and transition
• Focus beats everything: Why saying no to shiny objects accelerates growth
• The $200 ChatGPT investment that replaces a $50K employee

_

⏱️ Timestamps / Chapters

00:00 — Intro & dual childhood dream: military + entrepreneurship
03:00 — From SDR to founder: selling sensors → selling pet supplements
07:00 — 3Victor today: B2B go-to-market consulting & AI revolution
14:00 — Growth under pressure: The Dragons Den working capital crisis
17:00 — Strategic pivot: Self-funding through sales role (120% quota achievement)
20:00 — Behind Dragons Den: puppies, pin-stripes, and 45-minute pitches
26:00 — Cash flow lessons: "I didn't know fractional CFOs existed"
29:00 — Exit timing: friend's acquisition sparks the conversation
33:00 — Focus vs. shiny objects: The most common founder mistake
38:00 — Rejection philosophy: "Every great founder faces immense rejection"
44:00 — Rapid-fire: Zero to One & "Keep your cool under pressure"

_

🙌 Want more from AdaptCFO?

• Free CFO consultation
• Financial fitness scorecard
• Other episodes
• AdaptCFO case studies

_

Transcript

Eric: [00:00:00] John, welcome to the Growth Under Pressure Podcast. Super happy to have you here.

Jon: Likewise. Thanks for having me, Eric. I'm stoked.

Eric: Awesome. Me too. Look, so from the military to Dragons Den, that's not your typical founder's journey. Take us back to the moment you knew you wanted to build a business.

Jon: That's a good question.

I, it's funny, I, I found some old, uh, journals that I'd written when I was like, I think 11 or 12. But what I wanted to do when I grew up and the two things I wanted to do were go in the military and start a company. So I think I was fortunate to know that I wanted to be my own boss, young. Um, my dad had a big influence on that 'cause he was also an entrepreneur.

And so that kind of gave me, um, you know, like just a perspective that, you know, you can do this, you can build a company and live the life you want. Right? So just knowing that I think sparked that young and yeah, the military, I did, uh, four years in the, in the Canadian, uh, forces in the infantry and. Uh, I just, I always knew that it was, uh, like I, I wanted to go for a, a small [00:01:00] period of time, you know, life skills, experience, adventure, all that.

And then I wanted to get out and move on, and so I got out and got into sales and marketing and yeah, just I went from there.

Eric: Awesome. You know, I think a lot of kids, or you know, young adults need to go to the military to get disciplined, get buttoned up. And my cousin did the same. He was, I mean, sorry Ethan to call you out like this, but you know, he just wasn't making it in college.

It was different than high school. Um, high schools, depending on where you go prepare you differently, public, private, and also the actual high school itself. So do you feel like a lot of young adults need that? Military experience to, to step into the real world.

Jon: Yeah. I wouldn't make a blanket statement and say that everyone needs it.

I would say that for me it helped a lot and I think there are a lot of kids that would benefit from military service, even if it's just two or three years. I know I think most contracts are, are like three years minimum, [00:02:00] but I think that the benefits that you get from it are. You get to push yourself really hard, like beyond what you thought was possible.

And in situations that are pretty extreme and kind of crazy depends on the, the trade you pick, but everyone goes through basic training and then your, your trade training. And it just lets you meet people from all walks of life all across your country and just experience different things. So I think what I took away from it was the resilience and the.

Kinda that confidence of, listen, if I could do this, then I could go and work in a normal job and I could go and build a company. Like it just gives you that like confidence and like resilience and, and toughness I guess, in a way. Right? So, um, I also think for a lot of people it's a good way, at least for me, it was to go in and I knew within probably the first like six to 12 months that I didn't wanna do it long term.

Because of, you know, just the structure and the rigidity and all that. Like, I knew I didn't wanna be in that kind of career forever, and I wanted to have a lot of flexibility in how I work, what I work on, who I work with. So it was kind of a, I would recommend even doing it [00:03:00] just for people to know what they don't wanna do as much as what they do wanna do.

Right.

Eric: Mm-hmm. It sounds like it's really a, it was really a stepping stone for you.

Jon: Yeah, I think so. I, I'd say it was foundational to, to, you know, who I became.

Eric: And just for context for our users, you founded Bonnie and Clyde Pet Goods with your wife and grew it and went on the show Dragons Den, which is the Canadian version of Shark Tank.

And you, you know, you're, you have a founder's journey story. You also are a sales expert, in my mind, marketing expert. Now you have three Victor, where you're doing marketing consulting. So you know, with all of those. You know, of course with dragons then in mind, what was like that point in time, that inflection point where you're like, okay, I'm a businessman now.

Jon: That's a good one. Um, I don't even know if I still say that today, so, no, let, let me think. [00:04:00] Um. I was working in a sales job when I had the idea to, uh, to start my own brand, right? I was working as a, as an SDR, so like, just basically doing cold calling to these big companies, trying to sell sensors. I was working for hardware, uh, startup out of Quebec City, and, you know, that was where I, I first learned about prospecting and, and, you know, booking meetings and the sales process and all that.

And I just kept thinking to myself, if I can do this for someone else and make them money, like I could do this for myself. Right. And then, um, e-commerce was kind of exploding at that time. This was back in like 20 14, 20 15. So I had the idea of like, wow, you know, I can start an online brand. And then I had to pick like, which category and what kind of products.

And so I started doing research and I found that, you know, pet supplements were uh, you know, really high margin category, small, uh, volume and weight. So easy to ship. So really good for e-commerce. 'cause like pet food is heavy, expensive, so you have to go retail first right at the start. So I was like, okay, let's start with, uh, pet supplements online.

And if that goes well, I'll use my cold calling skills to get us listed in a bunch of retail stores and get [00:05:00] distributors. Um, so I think that the first time where I really felt like that would, would probably be, so when we launched and we had like the first sale come in, we launched on Amazon first in the US with, um, fulfillment by Amazon.

We basically like ship your product and store it in our warehouses. That first moment when we had our first sale and I was like, oh my gosh, a stranger found my product online and. Traded their $30 for my product. Like how cool is that? Right. Never met them in my life. And then it was like the first day that we hit five sales, the first day that we hit 10 20.

And it was like, you know, the numbers were just getting bigger, bigger and bigger. Um, that was a really, really fun time. And then, you know, that's the first kind of peak and then it goes down. 'cause you're like, okay, now this is working. I have to expand marketing channels. I had to grow more. You have to reinvest in inventory.

So all those like different lessons that you learn. I think the, probably the next biggest bump for me was getting our first distributor. So I just cold called, um, and I made a list of the top 20 distributors in Canada. Kept cold calling them over and over. And then about three months later, um, I got one, he invited me to come to a trade show.

We met, [00:06:00] I showed him a really crappy prototype of what our product would look like, looked like in retail. 'cause I, because we were online only, so it was shipping in like a bag with the, you know, the Amazon label on it, and then the bottle in it for the fish oil, for the, the dogs. So I took those bottles and I had this like, um.

Cardboard box, this really crappy white cardboard box made that was like a prototype. And then I, I printed out with a printer, an awful resolution. It looked so bad and I wrapped it around the, the box and I just walked up and showed him that. I, I, I was like almost apologizing, like, I know it's really ugly, but just imagine like a proper redling and everything.

And to his credit, uh, is Anthony, uh, elli of, uh, freedom Pet Supplies. He's a, he's a beautiful, uh, beautiful soul. He, uh, he just laughed and he's like, no, no, it looks good. Like I can see, I can see what it would be like. And he's like, yeah, come out to our office and ended up buying it. So that was the next big time was when I closed that deal.

I was like, we're going to retail, we're gonna get listed and, you know, hundreds of stores now thanks to this deal. So that was a big win. And I'd say the third big one was, um, yeah, dragons Den going on that show and yeah, getting all the dragons. I was [00:07:00] so nervous going in. And then my wife, I was like way cooler and calmer than I was.

But uh, yeah, we pitched, it went well and then we got offers from all the dragons and just coming outta there I was, you know, flying on, on cloud nine. Right. So that was a lot of fun.

Eric: That's amazing. That's amazing. Well, give us a little snapshot of today. What is three Victor, what do you, who do you work with and how do you spend most of your time?

Jon: Yeah, so three Victor is my consulting company for, uh, early stage, uh, B2B technology and services companies. I help them with, uh, everything that's go to market. So everything from uh, like strategy positioning, pricing, messaging, setting up outbound and content systems. Uh, I started working recently in the last like six months or so on paid ads as well.

So that's been a really interesting kinda experience to expand there. But essentially when early stage founders don't know how to. Like, which market they should go after or how to sell, how to position themselves. I help them work through that and then implement the systems to actually go and get customers.

Eric: That's great. That's great. And I, you [00:08:00] know, a lot about ai. It's, it's evident in our conversations in the past. I mean, we're always talking about ai. So do you think 10 years ago when you were, you know, head down doing research on the, you know, the pets, the pet goods and supplies arena, that, that would've sped up some time or maybe even.

Changed your mind, like how would AI have impacted you 10 years ago?

Jon: That's really good. Yeah. I, if I could go back 10 years with ai, yeah, I probably would've saved months of time and effort in like market research and. I mean these days you can just spin up chat GBT and you know, send a deep research prompt, like to find, you know, estimate market size and opportunity and all that to map competitors and find out what competitors are saying, right?

So all that work that I put in that was manual, I think it was good that I did it manually because I really understand everything that goes into it and how to do that kinda research. I've done it for a number of companies, but now having the knowledge of how to do it and how to prompt the AI and get it to do what I want [00:09:00] it to do, it's, yeah, it's night and day.

It just saves you so much time and every, it's crazy.

Eric: Yeah, it, it's, it's nuts. I, you know, I've done a ton of market research. Of course, when you're raising money for startups, you gotta find out what the TAM is, the total, total addressable market, and the amount of Googling that I did, and asking just the different sources where now you can just do some, like you said, deep search.

Um, or of course now it's GPT Five's Thinking model. Yeah. Uh, and of course there's a million different AI tools out there. Uh, yeah, the amount of hours it's saving people. Um, it is just, it's game changing.

Jon: Well, it's nuts. Those reports. Also, you can have all the citations, right? So you can still end up with like 25 to 50 sources listed at the end of the document.

So everything that you put in the document is defensible, right? And sometimes what I'll do too, to make sure that it's accurate, is I'll take the output, uh, research, uh, report, and then I'll say, I'll send another [00:10:00] chat and I'll say, fact check this report all the key claims and all the key data points and everything go and make sure that it's true.

And sometimes it'll cache little errors in there to make sure that it's actually, uh, accurate.

Eric: It's so easy too when you, when you see the answer and then you see the little, um, the little link for the reference. It's like, I, I actually just did this with the SBA, um, last week where it was like, hey, there was this publication that was released that says that SBA a's not charging 3% anymore, and it showed me the exact document and so I was able to send that to the lender.

Jon: That's insane. And. It's funny 'cause if you think about the value, like sometimes I hear people say like, I pay for the, the expensive version of chat gt like the 200 a month because I, I'm just in it all the time for my work. Right? And, but sometimes people are like, oh, there's no value in it. But if you think about like, just in your case, like, you know, using that to negotiate a deal, right?

And it saves you however many thousands of dollars your subscription's paid for itself already with [00:11:00] one. A use case or one task. Right. So I think there's, people need to be more creative about how they're using it and applying it. And even like asking the AI how we can help them. Like that's something, it's like a meta prompt of, hey, here's, here's what's going on, here's what I'm working on.

What are some things that I could prompt you to help me with? Right. And, and ask for suggestions. So, no, that's awesome to hear.

Eric: Can you speak on that a little bit more? The difference in that $20 package versus the 200 and maybe how, uh, you know, A-A-C-E-O or a business executive could, or, or even an entrepreneur, how they can prompt that $200 one differently than a $20 chat GPT model.

Jon: So I wouldn't say that the prompts between the models would change that much. I mean, there's probably some nuances, uh, if you have the different models, but for the most part it's more about like rate limits and having access to extra features. So I think with the pro version, the 20 bucks a month version, you only have a certain number of deep research reports.

Or deep research, um, searches. And also I [00:12:00] don't, I think you get limited access to the AI agent, but with the 200, uh, per month one, I, I have the, um, the AI agent, so I'll give you an example. We were, uh, looking for car to buy and I literally just made an AI agent prompt and set it and forget it for 20 minutes.

And I come back and I have a giant report of like all the different cars that, you know, would be a good fit for us, why it's a good fit, the safety ratings, like everything. So. I don't change the prompts between models for the most part. Um, but I, I use AI to improve the prompts, so I'll describe what I'm trying to do and then I'll say, make this into a better prompt.

And whether using the 200 or the, the, uh, 20 bucks a month version, that's a good practice in general because it knows the type of input formats that give it better results, right. Um, and the other thing that I do like about the pro version, um, or the 200 whatever, is you get the. Model's early. So you get to like test the new models before they come out.

Uh, publicly. I need to test new things, know?

Eric: That's awesome. Yeah. It's so, it's, it's more and, and deeper do, like, if you're doing [00:13:00] a lot of deep research, that's the model that you need versus more of a consumer every day. Quick answer.

Jon: Yeah, exactly. And another, um. Yeah. So in terms of like, uh, plan selection, yeah.

I think if you're using it on a regular basis and you hit the rate limits, then I would, it's probably, you know, worth upgrading. And also a lot of people think about it as a, like a software subscription, but I almost think of it as a replacement of a part-time or full-time employee. Right. So if you're using it enough, it's actually like buying you back a bunch of time that you would spend otherwise, you know, or someone that you have to pay however many dollars an hour to do that job.

Right.

Eric: Which is saving you thousands of dollars Exactly. At 200 a month. Great. I I'm really interested in the, um, I think it's GPT operator and some of those, like desktop take over your computer, um, a, you know, AI agents, which is, which is totally next level to not be, not even be hands-on and just, Hey, I'm just gonna speak, I'm gonna use like a whisper flow and just speak to it and it's [00:14:00] gonna do my work for me.

Jon: Yeah, it's. It's pretty crazy what they're able to do now. I think there's a version of that. So I know, um, operator, I tried out a couple times like make spreadsheets and go and research stuff and like, you know, build lead lists and stuff. But another thing that you can do is with, um. I think it's, uh, I think you can get a beta test version or something with the 20 bucks version where it has the, uh, AI agent.

So when you hit the plus sign and it pops up deep, you should see a new AI agent and you can try that. And it does like a virtual desktop in the chat and it can go really, um, it actually does better, uh, work for the most part than deep research I found. I've just started testing it out like this week.

Eric: I'm gonna try that. You gotta let us know and keep us updated how it is. Yes, sir. Great. Great. Now let's rewind to those first high pressure moments. As a founder in the early days of Bonnie and Clyde Pet Goods or, or throughout your career, what was your biggest, oh, no. Growth under pressure moment, [00:15:00] and how did you pull through it?

What was that? What, what did that dark time look like?

Jon: So the, the biggest one for me with Bonnie and Clyde was when it's actually, it's funny because you asked me when was the best moment, and one of them was Dragons Den. But it was also really closely tied to that, around that timeframe. So. Before, uh, after we filmed the episode, that was a blast, right?

Because we're, you know, had all these deals and then I was telling all our distributors, I, I can't tell you the results, but you should probably stock up on inventory, right? So I was like giving little hints and every, everything to my partners to, um, to buy more. But then in anticipation of the episode airing, I started buying a bunch of inventory and I was stocking up.

'cause our producer, um, really nice guy, Don, he told us that. Our episode because we're one of the first episodes filmed in the season. I, I guess the, the filming period is like five to six weeks long. And so I thought, um, and, and I asked him, I said, okay, we were like in the third or fourth [00:16:00] day of filming.

So given that we shot early in the film cycle or whatever, are we gonna appear probably early in the season? And he said, typically that's the case. So, you know, being a young first time entrepreneur, I was like, typically, yeah, that means yes, let's go. So I bought like way much inventory, but probably like, I think it was four times more inventory than I normally bought, because our distributor partners were saying that they were gonna buy a bunch and it was gonna be like this gangbusters thing.

So I bought a bunch of inventory and we were supposed to have the episode airing in October of that year. So we filmed in February and it was supposed to air in October. Turns out that our episode actually ended up airing in February of the following year. I bought all this inventory and I had all these payments due to our vendors and it was basically gonna eat up all the cash that we had left in the, in the company.

By the time that I had to pay them, because I negotiated, like I said, Hey, for this big order, I wanna split payment terms over three months. And they said, yeah, sure. Like gimme on Dragon in, this can be great. Right? So I negotiated like net 30, 60, 90, and so like the first net 30 payment was in October, and I was like, yeah, no problem.

Like we got the cash buffer for that. Then the next was in November, the next was in December, and so [00:17:00] this was like. In September, I was looking at my cashflow forecast and, and Don was like, I don't know when it's gonna air. And then October, I had the first big payment go out. Okay. Now I was starting to sweat a little bit.

Don, what's going on? When's it coming? When's it coming? Um, I think it's next week, maybe the week after. I don't know. So then by that point, I realized that if I didn't make a decision quickly, we're gonna run outta money. If I paid my vendors on time, I didn't want to be late on that, right? So I had this moment of panic where I, I realized.

I need to get a job 'cause we don't have enough cash here. And my investors didn't wanna put any more company, uh, any more money in the company until they saw how things were gonna take off afterwards. They're like, well, if things go really well, maybe we could put in more. So I was in this really tough position where I had to basically, you know, swallow my pride and say, well, I either, I stopped taking a salary from this company so I can make all my payments on time and have all my inventory so that we're ready for that time.

When, when the, in, um, when the sales pop. Or, uh, I just, you know, run outta money and you know, we basically go bankrupt. So I started looking for a sales job at that point and that was a really, really dark time. 'cause it was kinda embarrassing. You know, you feel kinda, kinda like a failure. [00:18:00] Um, and. You know, I had to get a job fast, I had to be remote and flexible.

So I keep working a little bit on the company, on the side just to keep it going, but you know enough that I can make good money and, and all that. So I ended up, uh, making a list of, um, like tech companies in Canada and the US that I thought looked cool and had good Glassdoor reviews. And I did this like research and I actually, this would've been a perfect use case for, uh, chat GBT.

Um, but I did this all manually. So I booked a list of like 120. VPs of sales and, uh, founders and just like cold emailed them, got like 20 interviews and then I got three offers and I picked the best one and started working with them as a, an account exec. I did that job for 18 months after that. So that was, uh, that was a tough period, like having the full-time job and the startup and the family life.

He had our first kid at that point, so my, my son James, so he's, uh, he's 10 now. But yeah, it was a, it was a wild period.

Eric: Wow. Wow. That really is a growth under pressure moment. And, and what ended up happening, did you, did you end up getting that sales increase, some growth where you were able to sell off the inventory?

A [00:19:00]

Jon: hundred percent. Yeah. So we were fortunate the shelf life of our product was two years, uh, if it stored, uh, good, good temperatures. So we had a warehouse in Montreal that was storing it. Um, then we had like a warehouse in the US that was storing it for the direct to consumer retail sales. And so for all the retail, uh, inventory in, in Quebec, we had two years to sell it.

And so I was a little bit worried that maybe if the sales didn't pick up after Dragons den, it would really hurt us. But man, when that episode aired that next, uh, the, the next week, we just, like sales took off and it went like that for an extra like two or three months where we saw a huge lift in retail sales and then it kind of settled in a, at a new normal level for us.

It was about a tripling or quadrupling of, of our normal, um, wholesale orders from our, uh, distribution partners.

Eric: That's great. Well, I'm glad you were able to get those, that inventory turned over. Otherwise that could have been, that could have been really rough.

Jon: Yeah. Yeah, that was tough. So that was, it was good.

We, we sold through that inventory I think in about, yeah, three months we had turned the whole thing and then we had other orders in the pipeline after that. So it was kind of funny to be like ordering this massive amount of inventory and, but then I'm also doing my sales job and like cold calling [00:20:00] strangers and trying to get deals in the door.

It was a, it was a really interesting period.

Eric: Sounds humbling.

Jon: Yeah, it was for sure.

Eric: So pitching on national TV is a huge moment. What is one thing that people don't. They don't see about Dragons Den or Shark Tank, um, on camera, you know, what is, what does, what does the backstage look like or some of the other nuances.

Jon: So, couple funny things that I didn't realize, uh, going in was, yeah, so they actually, uh, help you like. You dress up and everything, and so they, it's not like you're just going in, dress in whatever you want. They like advise you. So in our case, because our brand was Bonnie and Clyde, they suggested that we dress in like a suit and a, and an outfit and little bonnet and everything for my wife.

Um, pin stripe. Yeah. Yeah. Almost. It was, in my case, it wasn't pin stripe, but it was like I had a, a three piece, uh, outfits, like the suit with the vest and the hat, the like [00:21:00] mm-hmm. Pop hat. Yeah, it was cute. Um, so we did that and then so Don was helping us out with that. And then they do a lot of checks on you to make sure you're good and your microphones and all that.

Um, also there's a little bit of a blooper where in our, in our pitch, we, so we had to wait behind the stairs and we had, like, you could hear the dragons kind of talking about the last pitch, and that was a little nerve wracking. Like, oh, that was crazy. I, I never invest in that. You're like, oh my gosh, I'm about to go and fish to these guys.

Um, and then we, so you go out and in our pitch we had these, um, these dogs, these little puppies that we showed that had really nice coats. And it was a breeder in Ontario, uh, just outside of Toronto that had, uh. Been using our product for like about a year at that point, and their coats were just beautiful.

So the, the mother had been taking our fish oil product. It makes their, um, their skin and their coat like really shiny and, and nice. And so the puppies also looked super healthy. So we came in with a cart with all these little puppies and then these little doberman puppies, and then the Doberman mom came out and then ate the, um, the fish oil in front of everyone.

But it was really funny because she ran out, like ran past the bowl and it was like a bit of a blooper moment. [00:22:00] They, they thankfully edited that out and, and made it look good. Um, and then after that, the next funny thing that I found, or not funny but surprising was that the dragons were really, really nice.

They were not. Insulting or, you know, demeaning, like sometimes you see the highlight reels or like the, you know, the big fail moments. But I think there's probably a lot of stuff going on there that makes 'em frustrated with that particular entrepreneur. But in my case, they were, I found 'em to be super, uh, patient kind.

Like the whole pitch itself was probably like a 30 to 45 minute talk, and then it got trimmed down to like nine minutes in post-production. Right. So there's a lot of stuff that you don't see on the show. Um, but yeah, it, it was really nice. I just, a good experience overall. It's really, really stressful though.

Eric: Yeah, it, it looks stressful. That's interesting. 'cause I see, I, I mean, I haven't really watched Dragons then, except for your episode. I, I've primarily watched Shark Tank and I see, I've seen a ton of episodes and Kevin O'Leary is that guy that's just a hard ass and makes every life, everyone's life difficult.

And he just puts you down like [00:23:00] the little, if you have just a little shred of confidence, it just gets destroyed by him.

Jon: So hundred percent. I think we had a nice batch of dragons for that season. Kevin was at that point, I think he was down in the States doing Shark Tank. So for our season, we were in season season 11.

He wasn't, uh, he wasn't on there anymore, so I think we we're fortunate to, to miss that, but I'm sure Oh, that's right. Yeah.

Eric: I forgot he was Canadian, so he was on Dragons Den.

Jon: Yeah.

Eric: Yeah, that would've sucked. Glad you didn't I, I'm glad you didn't have to record in front of him. Agreed. Uh, so you ended up getting a commitment, right?

And, but you didn't end up taking the funds and you ended up going with another investor. Is that correct?

Jon: Yeah, so on the show we had offers from, uh, all five dragons. Four of them had paired up into two groups of two with different offers, but they were, they were all licensing deals and they wanted like 10 or 20% of revenue until their investments paid back, and [00:24:00] then a conversed to equity and all these like, complicated structures.

And then Jim Tring made us an offer for exactly what we asked for. So we just went with him. He was our target dragon going in there, uh, to start off with. And. Uh, coming out afterwards, we talked to one of his investment, uh, representatives, like the, one of the guys that manages his fund. And, um, yeah, we basically, they, they had to.

Their deal structure is that they get to have, uh, three months of exclusivity to consider the deal, and you have to give like a monthly report and like financials and all that, and you go through due diligence. But at that point, we were already in talks with investors that wanted to back the company, but they had kind of been, um, like, not stalling, but just like taking a long time to make a decision.

So when I talked to his investment representative, I said, listen, I don't wanna burn a bridge with these guys. Like they've been, you know, they've been good, like they've been invest, uh, and negotiating in good faith. So he encouraged me. He's like, listen, send us the, the updates, but you go, you can go ahead and finish your talk with them, and when you have a yes or no, come back to us and let us know what you wanna do.

So I called him afterwards, uh, the next day, um, went back home and I [00:25:00] gave him a ring and said, all right boys, we got an investment offer from, uh, Jim Tring, the, the founder of Boston Pizza. You know, uh, it's, it's time to, you know, make a decision, right? So that kind of got them across the finish line, and then they were like, okay, well why are the funds of this week or next week?

I can't remember what it was.

Eric: Awesome. So it's not, it's not always you, you don't always get the money that they, that you agree to verbally on the show.

Jon: Yeah. I, I'm not sure if I remember this correctly. I asked one of the producers, what's the percentage of like, investments that actually get done after the Yes.

And I think it was something like one in intense, like 10% of the deals actually go through afterwards.

Eric: Wow. And it's really just a marketing publicity play.

Jon: I think for a lot of people, yes. Um, I think a lot of times too, it's also the, probably the dragons that back out. 'cause I heard that a lot of founders misrepresent their numbers.

So on the show they'll say that they have 300,000 in revenue and then they look in the books and it's like, actually 200. And right there it's like, well that's a deal [00:26:00] breaker. Right off the bat you were dishonest kind of thing, right? Yeah.

Eric: Yeah, that's fair. So the episode air sales spike over what 300% in stores wanted your product.

You also, you know, you killed it. You got a commitment from, from one of the investors. You also had all five make offers. So what operational or financial fires did you have to put out?

Jon: Cashflow forecasting was probably my biggest pain point. I was. I was pretty good at calculating my margins. I, I didn't feel like that was a. A pain point that I had and we had only like one product, two SKUs. So it was pretty easy for me to pull the sales reports, you know, do some, uh, pivot tables, whatever, and excel and then, and then figure things out.

Um, but the biggest challenge I had was cashflow forecasting. I spent so much time in that 'cause we were so inventory heavy and we had to, you know, buy the inventory and then sell it. So just, you know, any growth that we had was tied with needing more cash to reinvest. Right? So we get these. Periods where we have so much, you know, cash in the [00:27:00] account.

But then I look at the inventory and we're down to our last like $5,000 of inventory. It's a cake so all the money goes back out. Right. So that's the, and I hear that's a common issue with like e-commerce and physical product companies is that kind of float as you're, you know, doubling and tripling in, in revenue is, is meeting that.

So that was the biggest challenge that I had.

Eric: Yeah, man, managing cash flow is absolutely key. And of course we specialize in it, so that helps. And, and I think a lot of people don't know about the fractional CFO model where you can get someone to even come in, like in your case and just do a quick project.

Hey, create a, a cash flow forecast for us and let us leverage it. Of course, you know, industries like CPG and uh, the hospitality industry have really tight margins. And yeah, it's hard to say, Hey, I'm gonna bring in this guy for $10,000 a month when I don't even have those margins to, to, to outlay that. So would you, you know, just looking back, would you have had one of those models created to help give you that

Jon: leverage?[00:28:00]

A hundred percent. Yeah. I didn't even know that was a thing. Like in my mind it was, there's an accountant and. That's it. Like I didn't know there was, it's either you hire like a, a high-end CFO, right? That I couldn't know, I obviously couldn't afford. Right. And or you work with an accountant, but it didn't feel to me like the accountant was strategic.

It was more just like, okay, you know, here are your books. Here's the end of your taxes, and that was it. Right? So there wasn't a lot of like value out there. Um, so yeah, I think going back, if I could, like, I could do everything again, it would definitely be to have like a CFO early on that would just give me their insights on like.

You know, Hey, here's how you can raise funding and 'cause all that. I was just kinda like reinventing the playbook, reinventing the wheel, so to speak, of like, what kind of funding do we need? Is it debt equity? How much do we need? Right? I was trying to do all that myself in spreadsheets, but the challenge I kept running was I would, I would do all these models and everything, but then I would end up questioning them if it was the best approach and I didn't know.

And sometimes I would turn to other entrepreneurs, but I never found that I got like great [00:29:00] financial advice from other founders. I dunno if this is a common thing, but like a lot of the founders I talked to were just more like, you know, uh, marketing or product visionaries, like focused on like the growth side of things.

They didn't really care too much about like the detailed ops stuff and a lot of 'em, they got to the point where their businesses were big enough that they just hired ops and finance people to do a lot of that work. Right. So I think it would've been a nice, uh, a nice stop gap or a nice like, you know, a partnership for a few years to have like a CFO come in, just gimme some ideas of like, Hey, here's what you need, you know?

Eric: Yeah. And come in at different times, right? Like in the acquisition or m and a phase, it's how can I increase my value? How can I showcase the numbers more? That's gonna get me a, a larger exit at the end of the day. So, you know, when you decided to sell the company, what made you confident it was the right move?

Was there anything specific?

Jon: Yeah, so selling the company, it was funny though. That conversation started right after I, uh, left my job, my sales job, to work full-time [00:30:00] in the company again. So at that point, this was like a year and a half after I had stopped. Um, while working full-time on it, I took that sales job and so I'd hit my quota actually was 120% of my quota.

And then I decided, okay, well, like the company's cash flow is enough to pay my living expenses. And I also, uh, had qualified, so my investors were gonna put more money in the company and I qualified for another, um, round of, uh, debt financing to, you know, launch a bunch of new products and really expand marketing.

So that was the game plan. And then right after I left my job to, to put this package together and I already got like, pre-approved before I quit. One of my buddies in the industry calls me up and says, Hey, my company's getting bought and the company that's buying me is looking an acquisition spree.

Would you sell? Would you consider? I said, listen, I wasn't looking for it, but we could have a conversation. So we had lunch and he started telling me about how it was working and that's what kinda sparked it. Um. I also had been in a bit of a place where I think I wasn't really enjoying the business anymore.

I wasn't interested in it anymore, and I don't know if it's because of that year and a half where I wasn't [00:31:00] working on it full-time and, you know, it was like just kinda steady maintaining both and not like, uh, not aggressive growth like at the start. So maybe I lost a bit of my passion and all that, and I was kinda like looking for another, um, another, uh, option.

So for me it was either like keep growing aggressively or get out. And then when the get out option was on the table, I was interested in actually pursuing it.

Eric: Do you have any regrets?

Jon: The only regret I have, and it's not really a regret, it's more of a disappointment. I don't regret the decision to sell, and I don't regret how I sold. My investors made a lot of money. Most of my deal was as like a, um, uh, not an earnout, but a, an equity swap in the HoldCo and that, and once I left that HoldCo after the acquisition, if the company kind of fell apart in the last couple years.

So it's not, you know, it's kind of a, a bit of a bummer, but. I'm happy I cashed out my investors. I'm happy that I made the decision to, to move on to other things because then I got to go into really cool opportunities afterwards. But I'd say my biggest like disappointment was that when I left the [00:32:00] company and I saw how they handled it afterwards, um, and I saw like, you know, consumer reviews that were like not great on the product because they're like, oh, you know, you guys changed something and it's not the same product anymore.

And I dunno what they were doing on the backend if they were changing the supply chain or whatever. Um, that was. So it's kinda like, it's kinda like your baby, you know? And then you have to see someone else do different decisions with it, and then maybe you don't agree with those. That was a bit of a bummer, but I mean, listen, at the end of the day, I sold and, and it was theirs to, to do with, uh, what they want, right?

Eric: Yeah. And this may be cliche, but hindsight's always 2020. You see an investment that blows up. You didn't put in enough money and you can say, Hey, I wish it would've gone differently. Or, but that's, that's really your path, right? And this is. This is your next chapter now, helping startups or small B2B businesses at three Victor work, you know, what's, you know, just pivoting a little bit here.

What's the common growth mistake you see [00:33:00] and how do you fix it? If, if you have any, any thoughts on that? Where do I start? There's a lot of growth mistakes.

Jon: Um,

Eric: just use me as a, as a use

Jon: case. No, no. I think that the biggest mistake that I see time and time again is, is a lack of focus. It's, it's trying to do too many things at once and across industries, across company sizes, across whatever.

It's like we find a growth channel that works and then, you know, someone says, oh, like we should also try this and we should also try this. And then we add in all these other things. But each new thing that you add in, and it's good to do to like growth testing, to be clear, I think you should test channels and see what works.

But when you find that one that works, all of your focus and energy and, and money should go into that channel until it's tapped out. Right? And it's kinda like an scur of growth. Like at the start you, you know, nothing's really working. You're, you're trying out a bunch of different stuff. Maybe you're. You try some paid ads, you try some outbound, you try some content, whatever, but then one of them, you'll, you'll get some signal, like [00:34:00] it'll work.

You'll get a little bit of a bump, and then if you keep investing in it, it'll really rapidly grow. And then eventually you'll get tapped out. Like at your next stage of growth, you'll hit your whole market or your ad response rate, like your, your CTR, um, your league will go up, your CT r will go down.

Whatever it is, you have to then pivot to a new channel. So it's, it's that lack of focus on what's actually working and just dumping down on that because, and I think Alex Zi talks about this, and I, I like this. He says that, you know, when you're an entrepreneur, you get rewarded at the start when you bet on yourself, when you quit something and start something new, right?

Your new company, you get rewarded with it, with customers and revenue and your independence. But if you keep chasing that, like quitting something and starting something new, you'll be perpetually stuck in the cycle of never just like letting growth happen. And it doesn't happen overnight. You have to give these things like three to six month cycles to like try and test them and make them work, right?

So I think that's probably the biggest, um, common mistake that I see. And yeah, it's shiny object syndrome, uh, at a, at a, at a basic, um, element of that. It's just trying new things all the time when you should [00:35:00] test new things, when, when you figure it out, exploit it and just scale.

Eric: Is there any out of the box advice you'd give to small business founder that's just getting off the ground that wants to get into marketing more than just reaching out to friends and family that, Hey, I would suggest do these three things to start, or even just this one thing.

Do you have some, do you have something? A hundred percent?

Jon: Yeah, I, I think. When you're starting out in a business, and it depends on the nature of the business, of course, right? I mean, if you're selling a consumer product versus a a B2B, you know, software or service or something. But, so I'll just, I'll speak to.

B2B mainly because that's what most of my experience has been, aside from my own consumer brand, right? I mean, even then I still ended up leveraging mainly B2B channels by selling through distributors. So I'll keep it B2B focused. I would say that the general solving order that I see work for founders of early stage, uh, B2B companies is outbound at the start.

Because you need to get revenue and you need to get leads right away. And the one of the fastest and simplest ways to make your stuff [00:36:00] known is to just send cold emails, send cold dms. Just reach out to people who use your product service and lead with some kind of value. Don't try to sell anything in that first email.

Just lead with like, Hey, can I show you a sample? Hey, can I do something for free? Can I give you a free, uh, report, a free audit, whatever, like, whatever your, your value journey looks like, your customer journey, fine. What that first thing is, and offer that for free and just do that. If you do that to a thousand people, 5,000, 10,000 people, whether you're using cold email, LinkedIn, cold calling, you're still very effective by one of those channels.

I'll do all three. Just pick one channel and just do it. For a month or two and then see what happens, and then try another channel after that. That doesn't work. If it works, just scale that. The second thing, after you get outbound working, at this point, you're getting calls. You have to make sure that you're actually converting them.

So if you have a, a gap in your sales skills, go and level up on that with some YouTube and some practice calls and all that. The second thing is content. You have to start putting up some content just to be present, because that'll actually help with your outbound. It generally won't generate leads in the first like month or two when you're still getting a feel for it.

But if you stick with it and you're consistent, [00:37:00] you'll build your following. You'll start having some inbound, like top of the funnel leads. If anything, the short term gain is that when you cold email or cold DM someone and they go and look you up on Google, Instagram, LinkedIn, you'll have a presence and they'll say, oh, this is a real business.

And they're, they actually have some good ideas, right? So your, your response rate will be higher when you have some, some content about you online. That's the second thing. The third thing, uh, is once you have those two channels cooking and they're, they're working well, you've grown, your revenue is to start with paid ads, start testing out paid ads.

And a common pitfall that I see with paid ads is people will try to test not enough. Not enough budget. And so the reason why paid ads is really nice is 'cause it's super scalable. You're basically doing, you know, uh, channels one and two, but at scale, like you can just turn it on when, whenever you want, you can just go and get leads.

So general cost per, per call metric is like two to $500 per, uh, held call depending on your niche and who you're going after. And so that's kinda the solving order. So start with outbound. Get your, your first sales calls booked. Get your first, you know, conversations and your first customers from that.

Figure out [00:38:00] what the objections are. Go rework your, your contents, your website, your social media profile. Um, start posting more regularly, and then eventually shift the paid ads once you have the budget for it.

Eric: That's awesome. That's great. So with the number one, the number one point you made, cold outreach, emails, calls, and all the above.

The main, the main blocker is rejection, right? It's, uh, those, those objections, those, um. Those just constant, Hey, we're not interested, we're not interested, we're not, how do you deal with rejection? I know this is more of a philosophical or personal question, but you've gone through it. I'm sure you've done tens, if not hundreds of thousands of cold calls.

How do you deal with rejection?

Jon: I just drink alone and cry. That's my no. Um, how I deal with rejection. So I think it's a mindset thing to your point. If you [00:39:00] look at, I, I started listening a few months back to the Founder's Podcast by David Sra. And I, I love that podcast. I think he does such a good job. He looks at all the, uh, autobiographies and biographies of the, uh, greatest founders in history, right?

So I had the, the biggest companies that persisted the most in time that had the most success, right? And a common pattern is that all of them had to face immense amounts of rejection. Whether it was, you know, Steve Jobs, or sorry, uh, Jeff Bezos going to a bunch of investors and having a hundred rejections, you know, whether it's, uh, David Ogilvy cold calling and sending, uh, direct mail to get his first advertising agency clients, right?

Every single founder has to deal with an immense amount of rejection. So I would almost frame it like how you deal with it. It's knowing that you will have to deal with it. What, how do you choose to, to internalize it and accept that you're gonna have to deal with it? Because there's no way around it to build a significant company, right?

Yeah. Otherwise, everyone's saying yes to you. It just means that you're, um, either you're not price enough, high enough, or you're not getting enough lead volume. 'cause you should be [00:40:00] hearing people rejecting you in your process.

Eric: Yeah. I remember in the early days of Adapt, CFOI called maybe like 10 to 20 people, and then I was over it.

I was like, okay, I'm not, I can't do this anymore. I just, I pivoted. Uh, it ended up working out and now we're, we are doing that cold outreach, as you know, and it's working and the, you know, it. The conversations go a lot differently when you approach them from a different angle, and I think it's also not necessarily getting your, that your head outta your ass and putting your ego aside, but you know, understanding that someone else has something else going on and you just jumped into their, into their day.

A so also just being empathetic to that. So yes. Quick pivot. What made your childhood different that brought you to the success that you've had?

Jon: So we moved around a lot. Um, I think that helped [00:41:00] me to see a bunch of different parts of North America and just get like used to, um, you know, really comfortable in different situations, right? And just talking to all kinds of people. So I think that was a really helpful experience and probably seeing my dad build his company.

The work that he had to go through. So my dad would sometimes have to travel for like a month or two when he was working on a new book. He was a, he was an author and he would do these books on different, um, different industries or niches. So he would say, okay, I'm gonna write a book on the gold industry in North America.

Right. And then he'd go and visit all these gold company CEOs and he'd basically like, collect our story and then like, put it together in like a 10 or 20 page chapter. Put 10 of those together. And you'd have, you'd have a book, right? Um. And so he was, he was a, you know, worked a lot. He was traveling a lot.

So I think seeing the work that went into building a company that, um, you know, basically provided for our family for 30 years, I mean, or 20 years, I think that's like a, um, that to me was a great mental model of like saying, okay, if I wanna do this myself, one, I know it's possible, and two, this is what it's [00:42:00] gonna take for me to be successful.

You know?

Eric: Um, can we go,

Jon: can we buy your dad's books? Are they in store or online? I think they're still on Amazon. Yeah. So on. If you search on Amazon for Michael Caldwell, you can find, uh, the books there. He's got some, uh, like the Great Fishing Lodge, uh, great fishing lodge's book is awesome. He had to fly to a bunch of luxury fishing lodges and do like these hunting and fishing tours.

And so he just got a bunch of pictures and wrote these really nice chapters. Um, he had the gold industry, uh, the uranium industry, a couple others like that. And he wrote, I think, I think he published like 25 books in his career.

Eric: Wow. I'll have to, I'll have to check one out. John. Those are some incredible lessons.

Let's close real quick with a quick rapid fire. That sounds good. You got it. Alright. Favorite business or leadership book you recommend the most? You can't plug your dad again 'cause you just did. So let's get, let's get another one.

Jon: Business or leadership book, one of [00:43:00] the. One of the books that changed my thinking the most was Peter Thiel's Zero to One.

Eric: Mm-hmm.

Jon: I really like that. Um, just the thinking of how you wanna build a business that is a monopoly, like a creative monopoly, and. How you, you don't wanna be competing. He had this analogy in there that really struck me was, you know, restaurants are not at all zero to one, right? Like, you're competing, not just with, if you start a a, you know, whatever, a Japanese restaurant.

You're not just competing with Japanese restaurants, you're competing with eating in at the house, and also all these other alternatives. For me, I found that really striking. So, um, yeah, I really like that book. It just ha I try to apply those kinds of lessons to whatever I'm working on, of how can I make something that's completely differentiated, even if it's only like a, a, you know, a small difference, but that adds a lot of value.

That adds some kinda like five or 10 x improvement in value for the end customer. And, and that was a big unlock for me, that book. I think that was really cool. One.

Eric: Awesome. Yeah, I have it. I remember I got that one for free and I read the first chapter, put it down, and I think I picked it up like 10 years later.[00:44:00]

And finish it. But yeah, it's a really good one. And quick, quick read as well. It's a, it's a small book. What's one metric you check every week without fail,

Jon: uh, leads generated. That's what I look at for most of my projects is I'm, I'm always checking in and seeing like, you know, how many leads were generated for each one.

So that's the, because I like to focus on the top of the funnel because if you figure out the top of the funnel, usually the rest of your funnel will take care of itself.

Eric: Yeah, absolutely. Complete this sentence for me. A founder under Pressure should always keep their cool.

Jon: So, um, that, that quote, uh, oh, sorry.

Rapid fire. I, I won't ya, we're good. No, tell me please. I want to hear it. Well, it's, it's, there's a quote that, uh. I can't remember the name of the actor, but he reads this passage from this book, and I can't remember the, the source, uh, book, but it was something like, if you can keep your, your cool when everyone around you is, is losing it, and if you can, uh, you know, put your head down and work hard and grind [00:45:00] through it and all this, like, I just feel like that it was really poetic.

Um, I think it was Rigid Kipling that wrote it and that was, uh, I just like that quote. So that's why I think if you can try to keep your cool when everyone else is panicking, that's a really strong quality for founders to have.

Eric: And it, it goes back to, you know, the cold outreach conversation, right? You just, you gotta keep your cool under failure and rejection at all times.

Awesome. John, this was really great. Really appreciate you having us, uh, having, you know, really appreciate you coming on. Um, me too. Is there a place that our listeners can find you?

Jon: Yeah, just on LinkedIn, that's like my main landing page these days. I, I just, my website redirects to my LinkedIn now, so yeah, just, uh, they can message me on there or, or email me at, uh, JN at three, victor.io.

Awesome, John, appreciate

Eric: it again.

Jon: Talk to you soon. All right. Thanks Eric. See you.

Eric: Cheers.