John SmallMtn (00:00:00)

Welcome to another episode of Founder’s Growth. My name is John Hill, AKA Small Mountain. I’m the founder of Adapted Growth, which is a coaching and training company. Today, we have a very cool guest on the show.

We have Jennifer Bleam. I’ve known Jennifer for a very long time. She is the founder of MSP Sales Revolution, and she works with IT companies in the MSP space to always keep them ahead of the curve. Thank you so much for coming on the show. We have such a cool history and I’m excited to dive into this with you. Can you talk a little bit more about how you’re helping people right now stay ahead of the curve with everything that’s happening and all the changes that are going on in business in general?

Jennifer Bleam (00:00:35)

Yeah, for sure. Thank you for having me on. This is going to be a ton of fun.

Yes, I do work with IT companies, and I help them walk into their small business clients, prospects, and community to identify AI opportunities. Where are there some workflows that need to be optimized? Where are some bottlenecks? Where are companies doing business as usual because a year or two ago, that was the only way to do things manually and sometimes laboriously? Identifying those and then bringing in AI solutions to solve some of those bottlenecks.

John SmallMtn (00:01:07)

Awesome. Very cool. We’ve been friends for a super long time, right? We’ve been Facebook friends, and then you did me a really huge solid a couple of years ago. You invited me to come speak, which was a really cool moment. How long have you been in the founder seat?

Jennifer Bleam (00:01:24)

About five and a half years. Five, five and a half years, something like that.

John SmallMtn (00:01:27)

Okay, awesome. What I would like to do is go back and look at those early, early days. When you think about your path as a founder, what sticks out to you as the places where you have had to figure things out the most, or places you’ve gotten stuck?

Jennifer Bleam (00:01:46)

Yeah, so let me start at the very beginning—a very good place to start. I thought my first offer was amazing, and I thought people would pound the doors down to buy from me. I do think it was a great offer, but the positioning wasn’t great. The messaging wasn’t great. I overestimated—maybe I underestimated—how much effort would need to be done on the sales side, which is so ironic as a sales trainer. So, that’s one thing.

Is it impossible? No, but if you’re a brand new business owner and hold onto that excitement, the newness, the dream, and the vision, all of that is great, but understand that it might be tough. It might be harder than you’re expecting. That is a very good lesson to learn, which is one of those things that seems to come back whether I’m learning Facebook ads, learning a new prospecting approach, or maybe learning how to expand into Instagram—which is something we’re considering for a few months from now. Everything has a learning curve, and I think that there is a direct correlation between how much you can lean into that uncomfortable newness.

“I don’t know how to do this. I’m very much aware”—you know, the conscious incompetence. “I do not know this thing at all.” When you’re intelligent, you’re well-spoken, and you have a great reputation in the community, but there’s this thing that you’re trying to learn, it can really eat at you if you’re not careful. So, being careful to separate your identity from your results is super important. The longer you can stay in that incompetence and just sit there, learn, iterate, and try…

I like to use the word “hypothesis.” My hypothesis is: if I do this thing, then I think I will get this result. Somehow, naming it a hypothesis takes the pressure off, and it’s almost a bit of gamification.

Let me give you a case in point. This was probably last July-ish. We had a hypothesis that if I used an AI-created headshot with every one of my text posts on social media, our reach would go up. Indeed it did. Our reach doubled because of putting an AI headshot. It’s a pattern interrupt. People are scrolling: today Jennifer’s baking bread, tomorrow Jennifer’s outside, the day after that she’s in the rain, the day after that she’s in London, the day after that she’s sitting at a desk, the day after that she’s on a podcast. That hypothesis happened to work. Had it not, we would have gone to the next hypothesis, and the next one.

The longer you can sit in that uncomfortable, messy middle—”I am incompetent and I know it”—the faster you’re going to get to the next level, which is conscious competence.

John SmallMtn (00:04:46)

Yeah, conscious competence. Framing it as an experiment was such a huge lever for me, because I have a high need to be right and make sure that things go well. It’s super easy to want to build a plan in the lab without really testing it in the field.

Now it’s funny because in some of the books I read, I can see people talking about this idea, and I’m like, “Where was this seven years ago when I started?” It was in those books; I just hadn’t read them yet.

Jennifer Bleam (00:05:21)

Yes, or the concept of “launch before you’re ready.” If you’re happy with the software tool that you launched, then you launched too late. That one is something that I’ve just learned in the last year. I was really good at rearranging all the things, whiteboarding all the things, and needing to have a perfect onboarding sequence before anyone had even bought the offer.

I have learned this last year to just get out there and say, “Are you even interested in this?” If enough people say no, then there’s a problem with my offer. That means I don’t need an onboarding sequence, because no one’s going to buy it, or not enough people will. Then separating those results from “I’m a failure because nobody wanted to buy the thing.” No—retool it, remessage it, add more value, change the pricing. All of the things. Iterate, just iterate.

John SmallMtn (00:06:07)

Yeah. One of the things that you talked about before was getting started. We’ve all got big ideas and visionary beliefs. We all think it’s going to be different for us, and that can lead to struggle. Other than framing things as experiments, how has Jennifer gotten better at analyzing new ideas while keeping in mind that there’s a learning curve? Do you have any other tips, tricks, or anything that you have found helpful to make sure you’re going into new things with your eyes wide open?

Jennifer Bleam (00:06:48)

Part of it is remembering that you’re not married to this idea.

I was talking to a friend maybe three months ago, and we were putting together a new offer for me. He said, “What about if you do…” I don’t remember what it was—daily Q&A calls or something. I’m like, “That sounds awful.”

He’s like, “Okay, what about weekly?”

I’m like, “Maybe.”

Then he said, “You know you could try weekly, and then if you don’t like them or people aren’t showing up, you could just change your offer.”

I was like, “Of course I can, because it’s my business.”

So, I’m not married to this. That is one thing: don’t feel like you’re married to your first idea. Your first idea might need 15 iterations before you find the thing that you land on. Even once you land on it, it’s selling well, and you’re hitting your revenue goals, it will flex. You may need to add new things. The market’s going to change. Now AI is huge; in five years, it might be robots. Who knows? Don’t get too married to an idea. Let yourself be flexible.

I’m going to add this: everybody isn’t cut out to be a business owner. That’s not necessarily a bad thing. It’s only a bad thing if you spend 25 years trying to run a business and now, all of a sudden, you’re however old and you’re like, “Oh, I never could make it work.” That’s okay, but let’s try to figure that out early in the journey.

Many people had failed businesses before they went back to the workforce, or three failed businesses in a row. It gets easy to see all the people with large businesses, successful businesses, or serial entrepreneurs because that’s what people post on social media. Nobody posts, “Hey, I just filed for bankruptcy. Wish me luck!” That’s not what we’re seeing.

When we might have that happen… I have a family member who had to file for bankruptcy in the last year, and she felt very alone. I’m like, “Hold on, just statistically, look at how many people have to file bankruptcy. Look at how many people have a failed business.” Again, it doesn’t mean you’re a failure. It just means this business, this timing, this offer, or this niche wasn’t the right time.

Everybody isn’t right for business ownership. Draw a line in the sand. “If I’m not making this amount of money personally, or top-line revenue for the business, by this date, then I’ve got to make a hard decision. Am I going to try for one more quarter, two more quarters? Am I pulling the plug and going back to the workforce?” Neither one of those is a bad solution. I think the bad solution is just living the same year over and over again and not making forward progress.

John SmallMtn (00:09:43)

Absolutely. Even in there, there’s a bit of an experiment: “Here’s the mark of success. Here’s what’s indicating that this experiment is working very well.” Like the scientific method—have a hypothesis. I love that.

One of the things we talked about was drive. You’re a D-type on DiSC, right? That means big goals, moving fast, hard values, and “let’s win.” You and I have talked at length about this. One of the things we were talking about was being able to slow down and appreciate progress and the journey, rather than being so focused on the destination. How do you balance between those two things?

Jennifer Bleam (00:10:26)

It’s not an easy balance because, as you said, my natural bent is, “Let’s go a million miles an hour.” But with age comes a little bit of wisdom, I think.

I’m now able to say, “Okay, I wouldn’t be where I am today…”—one of the biggest thought leaders in our industry when it comes to AI. I’m getting tagged in conversations. I’m getting more collaboration opportunities than I can deal with. I just had to shrink my calendar block to where I cannot see people for three months. I just can’t do it.

I was an overnight success that took five years to get there. Even before that, right? I wouldn’t be able to talk about sales, and I wouldn’t have the relationships that I have today, if I hadn’t written the book on cybersecurity selling, hit the bestseller list, and done the whole podcast circuit. It’s a sequential thing. Those all became building blocks.

I didn’t wake up one morning and have the reputation, the courage to step into AI, and a great series of inner-circle and outer-circle people that I could text and get answers from tomorrow. That doesn’t happen overnight. That happens in the trenches as you’re building, iterating, and testing hypotheses. Some succeed, a lot don’t, but you have to be doing. You have to be trying, not coasting.

Being able to say, “Okay, none of the failures in air quotes were bad.” Any failure I can point to, there were lessons there. I think it’s bad if you fail and you don’t extract the gold, and then you turn around next quarter and make the same mistake. Part of my D personality is that because I’m going 100 miles an hour, I can’t afford to make the same mistake twice, because I’m going to hit that brick wall really fast.

I do try to be disciplined with, “Okay, this didn’t work. This offer didn’t work. Why not? What’s my hypothesis on why it didn’t work?” Then understanding that even if, let’s say, I wrote a book and it didn’t hit the bestseller list, and I was only on two podcasts and nobody wanted to hear from me, that’s okay. I still would have gone through the process of writing the book, which a lot of people haven’t done.

I know you have, but many listeners probably have a book idea in their head. We were both writing books pre-AI, so we wrote them the old-fashioned way with voice, a typewriter, or a keyboard. There were no shortcuts. Even that was a learning lesson. I had no idea how to do those things, and I leaned into “who, not how.” Who can help me get my manuscript from 40 Word documents—I kid you not, a Word document for every chapter, Word documents for chapters that got thrown away, and a Word document for cover ideas—and then I just hired someone and said, “Here is my mess. Here are my 40 Word documents.” I paid her, and she got it over the finish line.

All of those things are lessons that I can now build on. That’s a “how” method—setting a goal and making it happen. So, yeah, it is about the journey. The destination is fun too—setting goals and hitting goals is a piece of it—but the journey is important.

John SmallMtn (00:14:01)

Yeah, I was calling mine a “word baby.” It was weird because normally everything I write, I ship off to Melissa, my wife, who’s my editor. But this felt different, and I wasn’t really sure exactly what it was going to be. Then I finally let her read it, but I was calling it a “word baby” because I didn’t want to put weird constraints on the idea. I didn’t want to call it a book if it wasn’t meant to be a book. It could have just been a manifesto or something else. It could have been a number of things.

So, I was savvy enough by that point that sometimes the label creates some of the constraints. I was trying to be very open with what it could be.

Jennifer Bleam (00:14:44)

Nice.

John SmallMtn (00:14:46)

Now there are so many AI tools and people that can get through the process a lot quicker. In my opinion, that doesn’t diminish it. I’m not trying to gatekeep writing and stuff like this, because it is a hard journey and a lot of work. It’s going to show you where your blind spots are, which is a really helpful thing.

Changing gears a little bit: one of the things that we were talking about that kind of shocked me was that you don’t do to-do lists; you have “to-don’t” lists. Can you talk a little bit about that? How do you manage that? What does that look like for you as a working process, and how does it help?

Jennifer Bleam (00:15:22)

Yes, yes. I do have a to-do list, but I always look at it through the lens of my to-don’t list. Let me talk about the weird one first—the to-don’t list.

This was a Benjamin Hardy idea. I took his idea and tweaked it for my own. It’s a pivot on the 80/20 rule, like the Pareto principle, right? 20% of what I do as a founder gets me 80% of the results. So, I literally listed everything that I was doing. This was probably two years ago, and I don’t know if I had a team. If I did, I had a part-time executive assistant and me.

As you can imagine, that list was very long. I think I ended up with 45 tasks that I did in a given month. Then I did the math. What’s 20% of 50? Okay, that means I can do 10 of these, right? So, I have 10 of these.

I did this on an airplane. I think really well on an airplane. The hum, nobody can interrupt me, I always get a window seat… Nobody can interrupt me and I’ve got my tray down.

I’m like, “Okay, I’ve got 50 items. They all need to be done, but there’s only 10 that I can do. What are they?” The first three or four were really easy, and then it got hard. I just circled them—nothing special, right? Then I was like, “No, I can’t do that one. I’ve got to do…” It was kind of tough work.

Then I sat with that 20% and said, “If I spend 40 hours a week doing this”—or maybe it’s a short week and it’s 30 hours a week—”would I like this life, or would I be ready to kill myself?”

I was like, “Yeah, this would be a lot of fun.” Being on podcasts was one thing. Studying trends in the industry was something else. Coffee conversations… There were certain things that only I can do. I can’t outsource podcasts to a team member. So, I sat with, “Would I like my life?” And I’m like, “I would love my life.”

Then we put a plan in place. We just called it “80/20 Jennifer’s Life” or something like that. Every quarter, we go through and say, “Here are the three things we’ve got to offload. How does Jennifer do this task? How does Jennifer think about this task?”

Magically—a little sarcastic there—because I am purposefully spending time on the things that move the needle, the business needle started to move. Now, I am not perfect. This week, I’m onboarding a new employee, and I’m getting pulled and interrupted a lot. There are seasons. I’m fighting a bit of a cold, so this has not been my best week ever. I’m not perfect, but I’m always filtering it through the lens: “Is this something I should be doing, or could I send it to a team member?”

I have two team members—a pretty small team—and then I have some people that I outsource random tasks to on Fiverr, Upwork, and stuff like that. But I make my to-do list, and then I circle the things I’m going to give to a team member. I look at my to-do list, and once that is off my plate and my shoulders, I feel the weight lift just a little bit.

Then, what I do is try to identify the one thing that is the most broken in my business and go all-in on that one thing this week. That’s the process that I use because I’m a big systems and process geek. Every system is perfectly designed to get the result it’s getting. If I don’t like the number of leads coming in, it’s because my system is creating that number of leads. If I’m not getting enough sales calls, it’s because my sales system is generating that number of sales calls. I can’t fix everything every week, but I can identify the worst problem—the biggest problem—and solve that to the best of my ability. Rinse and repeat that every week or every other week, and you’ll solve 25 to 50 problems a year, which is great.

John SmallMtn (00:19:54)

Yeah, absolutely. I love the idea of building the list first and then chopping it down from there. I think a lot of people get stuck when they do these kinds of ideas, whether it’s the Dan Martell stuff or the Who Not How stuff, however you’re thinking about it. It becomes very easy to be like, “Okay, this is my zone of genius, and I’m only going to be doing these things.” That’s a version of the inner critic coming through. You might be creating massive blind spots because you’re just thinking about what you’re going to do.

I love that idea that you still build the list, and then you cull it down after you have everything out of your head. That’s something that would trip up a lot of people because they get very focused on all of these different business methodologies and ways of thinking.

The other thing you said was that you took something from Benjamin Hardy and needed to customize it for you. Every one of these systems has got to be customized for you. Now, I think you need to run it in its pure form enough to really understand what needs to change, because most people are going to come in with their own biases and blind spots and want to change it too much.

I like EOS a lot, but eventually, you’re going to have to take it off the shelf and realize that they didn’t make that specifically for you, and try to take it off-road so it fits your thing. There was this line in martial arts that we always talked about: people that do mixed martial arts versus one style are cherry-picking things that are easy for them to do or that they’re excited to do, as opposed to learning a whole system and then thinking intentionally about what the gaps are for you, doing it enough that you’re not lying to yourself about any of these things.

Jennifer Bleam (00:21:41)

Yes. Well, because once I identified, “Here’s the 10 things that only Jennifer can do,” those other 40 things still had to get done. The business will grind to a halt if somebody isn’t tracking the metrics and feeding them to me.

That’s the other thing that I’m saying: okay, I would love to offload all the 80%—the 80% that is necessary but isn’t urgent, isn’t important—but I don’t have the team where I can just offload all of it. There are things that have to continue to happen.

One of the things we’re working on internally, I call it pushing the data to me instead of me pulling the data. I like to track the numbers. I do not like to try to find the spreadsheet to look at it. Part of what my team does is track specific numbers, and then they send me the link to the spreadsheet. I don’t have to make the stop to go look at the spreadsheet. Instead, it’s in their end of shift, “Hey, I updated the numbers and here’s the link to the spreadsheet.” Push the data to me, because I know my weakness: I get busy, I still have a long to-do list, and I’m going to be like, “Ah, I’ll just look at the numbers next week.”

Then, all of a sudden, next week becomes next month, becomes next quarter, might become next year. I’m like, “No, we’re tracking the numbers. Why is Jennifer not looking at the numbers? Oh, because she has to find the spreadsheet,” which sounds so silly. But identifying, again, where’s the bottleneck in the process? In this case, it’s the human—it’s me, the human in the loop. How do we fix that? How about if I just have my team message me the critical numbers or message me the spreadsheet? We’re starting to go, “Please push the data to me. Don’t make me go pull the data.”

John SmallMtn (00:23:17)

I think some people would hear this and be like, “Are we being a little picky?” But if we’re trying to get a lot done, which is required if you’re to run a business, you have to be looking for those little things, right? Because awareness matters more than the land of “should.” I tell everybody the land of “should” is like… you should not be living there.

If you’re aware enough to know that, “I love data, but I’m resistant to building all of this stuff, it puts me in perfection mode, so just ship it to me so I can look at it,” right?

One of the things that I talk about with salespeople that are reporting to a head of sales or reporting to the founder: allow that person to function as an executive, right? Give them everything they need to make a decision. Don’t put a bomb in their lap and then be mad at them that they weren’t able to go fix your problem when you didn’t give them enough to be able to be like, “Okay, here’s some options for me, A or B.” My gosh, right? Awareness is such an important thing, and just owning it. I love that.

Jennifer Bleam (00:24:28)

I know this system is going to break because of me. So, let’s fix it. Let’s not let it break. I don’t want to get to the end of every week and be like, “This week was great, except I didn’t look at the dashboard again.” Okay, then let’s make it easy. Let’s set the dashboard as my homepage so when I open my browser, it’s right there.

We’re looking at some AI tools because we use CRM ActiveCampaign, and it doesn’t have any great dashboarding. But I can pull the data out with Zapier and push it into a Google tool where I can build a dashboard. I’m like, “I have wanted a dashboard for so long.” That wasn’t a compelling reason to leave ActiveCampaign; there may be other compelling reasons to do that. But I need it in my face because I am not going to be disciplined. I’m disciplined about other things, but I’m not going to be disciplined to go find the spreadsheet because it’s 11:15 and I look at that every day. I’m just not there to beat myself up and be like, “You should have more discipline,” and whatever. I’m like, “Okay, but I don’t. Maybe I should, but I don’t.”

So, let me create the system that factors in Jennifer’s weakness of not having discipline. Let’s just own that, figure out a workaround, and move on. We have too many other problems to solve.

John SmallMtn (00:25:37)

Yeah, no one’s running perfect in 360 degrees. It’s absolutely absurd, right? Man, I run into… I mean, myself as well, right? Just yesterday, we had a new guest coming on, and I was super excited, right? I’m working with a consultant on this thing, and also working with my wife. My wife was like, “Hey, did you put that in ClickUp?”

I’m like, “I need to go put that in ClickUp,” right? I’m not going to be perfect, and I don’t try to make any allowances for it. This goes to the other thing: you need to have people who you trust enough to push back on you in those moments, as opposed to letting your ego run wild. “Well, I’m the founder. You can’t tell me what to do.” Get people that you trust enough to hold you accountable to the processes that help everybody. The little mini-tyrant running around with no one being able to tell them no is going to be problematic, right? You’re going to hit a lot of ceilings and you’re going to burn through a lot of people, which is not helpful.

Changing gears a little bit, I want to talk about the “easy button,” right? Because this is a thing you talk about a lot, and I respect that. A lot of people are seeing AI as the easy button right now. Can you talk a little bit about how people chase easy buttons, and how AI can be super helpful, but it’s not a silver bullet any more than automations were a silver bullet, any more than CRMs, cloud computing, and Salesforce were silver bullets? How does that show up for you as a founder? How do you make sure that you’re not chasing shiny things yourself?

Jennifer Bleam (00:27:31)

Yeah, so let’s back up and first prove that there is this concept of the easy button. All you have to do is go to YouTube, refresh the page, and you’re going to see… I haven’t counted it, but I would bet one out of every three videos is going to be like, “Just use these four AI tools to change your business.” “Just do this one thing in your sales process and you’ll close a bajillion dollars tomorrow,” right? “Let’s do this one thing to your marketing funnel and all of a sudden you’ll be swimming in leads.”

That’s sexy and it sells, but that’s not really real life. Real life is it comes with complexity. To try to figure out how complex your business is, all you have to do is try to whiteboard out workflows and be like, “Okay, well our social media does this, and it leads to the lead magnet, which does this. How many tools does that involve? How many automations is that? Are you using Zapier? What things could break?”

Complexity is part… I’m good at making things very complex, but that’s because sometimes they just have to be. We did a launch a month or so ago, and on the first day of the launch, something went wrong. One of the tools stopped working. My team came to me and they’re like, “All we know is someone bought and they didn’t get the tag.”

I’m like, “Okay, which tag did they not get?”

They told me, and I said, “That’s a problem with Spiffy,” which is a Stripe add-on, because Stripe can’t add tags, but we have to add tags in order to onboard people. So, we need a second tool to add tags.

My executive assistant was like, “Well, are you sure it’s not coming from Jotform and Zapier?”

I’m like, “I’m positive, because that happens after the sale.”

Just to run that launch probably used 10 tools. We have it charted out in Canva with Post-it notes and all of these things, but it is complex.

That would be my first word of warning: when you hear from a seller or a marketing person, “Just do this one thing and it’s going to revolutionize your content generation, your close rate,” fill in the blank, that should raise red flags. I’m not saying everything has to be hard, but very few things are that easy. If there was one thing to solve everybody’s sales problem, then neither John nor I would have a business because everybody would just put that one thing in place—whatever it is: a form, a widget, the magic question, the one-page slide deck. There isn’t a magic easy button.

When you hear that… it’s tempting to want that. You can burn a lot of money and a lot of time going, “I have the magic prospecting kit. I have the magic sales process.” I’ll be like, “Cool, I’ll buy that from you. Cool, it’s only a thousand dollars a month, I’ll buy it because I think that’s going to solve my problem.” Then all it does is add complexity and make it hard for me to lean into my gut, and I’m now leaning into the expert. Why? I guess the expert knows more than me. Not always. So, just be cautious of that easy button, whether it’s a software or a solution. Expect there to be effort.

John SmallMtn (00:31:10)

Yeah. One of the lines that I have been using a lot as a reminder to myself and with my clients: don’t expect this to be easy; it needs to be worth it. Because if it’s worth it, and that means understanding your goals and understanding where you want to go, then you’ll show up ready to work through it, as opposed to just being mad.

To that point that you were talking about a second ago with the tools in the launch, it would have been super easy to sit and spin your wheels trying to find that one system that could do all those things. Then you’re taking demos and you’re just opening yourself up to someone showing you a shiny thing, as opposed to, “What is the use case? What does this need to do?”

Diagram your stuff. Think it all the way through. This leads to that, which leads to this, and what happens if this happens? It’s not sexy and it’s not fun, but you’re going to move so much faster if you just decide to slow down a little bit and think all the way through the problem, as opposed to just thinking that technology is going to make it effortless.

Jennifer Bleam (00:32:19)

Yes. Add a buffer into your project. I have a colleague who just switched to HubSpot from… I don’t even know what tool he was using. It was slightly more expensive, and then some things didn’t come over right. He had to rebuild or try to find out what wasn’t working, so he had to hire a consultant. The migration ended up taking longer than he expected. He had to hire a consultant, which was not originally in the budget, but the end result was still that he got migrated to HubSpot.

Now, he was smart enough to not get wooed by someone saying, “I can make a HubSpot migration easy.” Maybe there are those people out there—I’m not saying that doesn’t exist—but if you are starting to hear things that sound too good to be true, they probably are not.

John SmallMtn (00:33:13)

100%. When you’re thinking about the things that you’re going to try… because I know that you’ve run events, and you’ve been talking about ads and different things like that. How do you prioritize what you’re going to actually run with? Because I imagine, like myself and a lot of other people who come on the show, when you get into this mode and you’re here for a while, ideation becomes easy, right? You’re networking and you’re hearing from other people: this person did this and it helped, this person did this and it helped. How do you put and keep focus on the things that you’re going to prioritize?

Jennifer Bleam (00:33:55)

I ask, “So what?” Let me say I do this thing in an event, I start a podcast… So many ideas! Like you said, my whiteboard is covered; it’s pretty crazy. What happens if I do this and it works? Does it get me closer to my end goal? What happens if I do this and it doesn’t work? Are those going to be lessons that are helpful that I can carry into something else, or are they kind of one-off lessons that only apply to that narrow silo?

That’s part of how I look at what I’m focused on this quarter or for the next six months. The other thing, because of that 80/20 rule and not wanting to add anything to my plate… I wrote down, “It’s not easy, but it’s worth it.”

We are redoing our entire prospecting system. My plan—my hypothesis—is that I can create this system over the next 90 days, put an hour a day into this prospecting system, track what works, and figure out messaging so that I can bring on a salesperson. That is something else that I look at: am I doing a thing in such a way that I can offload it, or am I doing this thing that I will forever have to own? I’m not trying to create a job. I could go out and get a job tomorrow, probably. I don’t want a job; I like being my own boss.

That’s another lens that I look at things through: over the next 90 days, we are going all-in on this concept of a sales power hour, where every day we work for an hour through a process that right now is in my head. By tomorrow, close of business, it will be documented, at least on a whiteboard. Then, “Okay, that’s what I think will work,” but we need scripts, talk tracks, and checklists in our CRM—all of the operational things for that process, so that I get this end result and then I can forklift it over and give it to a team member.

John SmallMtn (00:36:08)

Nice, I like that a lot. I want to talk about events for just a minute, because I know you’ve hosted an event and I got to speak at it. It was such a cool thing. The IT MSP space is riddled with events. What are the biggest lessons you learned from hosting an event?

Jennifer Bleam (00:36:25)

Yeah, it is. Man, we could probably talk about that for two hours.

Getting butts in seats is very difficult. However hard you think it is, quadruple that hard, and you might be close… maybe.

You figure travel, maybe there’s a ticket cost, “I’m away from my business for x number of days, I’m away from my family for that same time period. Is this going to be a pitch fest, or is it really going to be valuable?” All of those questions are in the mind of the prospect. You have to answer all of those questions in order for them to purchase the ticket, and they can’t have anything else happening on the same day as your event. So that’s one thing.

The second lesson is that events are complicated. If you ever attend an event, step back and realize: somebody had to figure out what color the spotlight was, how tall the stage was, where we are getting AV from, how many microphones we need, are we going to have lanyards, are we going to have name tags, how do we register people, what time is this session, how do we stay on track, is there a confidence monitor? The number of questions and logistics to run an event is obscene. I don’t even know how to explain it.

If you and your team can’t handle that level of detail and those numbers of questions, then you need to hire an event coordinator for probably $10,000 to $15,000 to answer all of those questions for you. Except then, they have to be able to read your mind, or at least capture your vision and translate it to all of those vendors and manage all the contracts and things like that. So, it is valuable, but it is a heavy lift.

John SmallMtn (00:38:15)

Interesting, okay. Talk about a shiny thing, right? And thinking that it’s just going to be easy. “Well, I love events, so therefore everyone’s going to love events. Everyone likes me, so they’re going to come to mine and they’re not going to go to their kid’s graduation, their kid’s soccer game, or the other 17 events that are going on on the same day.”

That’s a nugget: it’s going to be harder than you think it is; it needs to be worth it.

Jennifer Bleam (00:38:46)

It’s interesting because I had someone approach me a couple of weeks ago and say, “We’ve got this great idea for an event in the space, and we wanted to see if you wanted to do this with us.” They had the idea. I love the idea, and I like the people. But their idea was, “We don’t want to sell sponsorships.”

I said, “Okay, well how are you going to pay for everything?”

They’re like, “Well, I mean, we’re going to sell tickets.”

I’m like, “That’s a problem.” I said, “Listen, I’m not trying to rain on your parade. I’ve done this three or four times now for my own event, and I planned probably five events before that that weren’t my own.” I said, “The problem is you have to pay half down, and half on the day of the event, 60 days before the event, when you haven’t sold a single ticket yet—or maybe you’ve sold three or four. Can you front-load $50,000 in the hopes that you sell $100,000 worth of tickets?”

That depends on the size and scale of the event, but that’s roughly what the numbers are going to look like—maybe a little less, but certainly it can go significantly up from there. Some people have million-dollar events. It’s easy to go in and be like, “Everyone will come to my event; they love me.” But they love their child who’s graduating, or their wife who’s like, “You traveled so much last year, honey. You promised you weren’t going to travel as much.” There’s all of that happening that you can’t control. So, it’s tough. It’s a tough gig.

John SmallMtn (00:40:19)

And I know you ran your event for multiple years in a row. I’m curious: what was the biggest lesson that you worked on, put a hypothesis around, and ran an experiment on between year one and two that had the most impact?

Jennifer Bleam (00:40:50)

Between year one and two, we did a great job pre-selling tickets for year two. That gave us some cash flow to be able to put the deposits down and things like that.

So that’s probably one of the biggest lessons. The other big lesson is just the logistics—especially the sponsors. The person you’re talking to, Richard… then Richard’s not in the company anymore. He got a new job, so you’re scrambling: “Who took Richard’s place? Who’s my new point of contact?” It’s just the communication. There’s a lot of communication.

John SmallMtn (00:41:23)

I just remembered this: I remember getting on site at the hotel, and I ran into you. You were talking about how all of your stuff had been shipped down and it was locked away, and you were trying to get in so that way you could have all of your signage and all of your stuff for this thing. No one plans for that kind of stuff, right?

Jennifer Bleam (00:41:38)

No. We literally shipped everything ahead of time and we rented a storage locker. The day before the event, the plan was to go to the storage locker. We had hired a moving company. We were going to unpack the storage locker into the moving van, bring it all over to the event site, and have it staged for the people to pick up their things and set up our things.

I’m trying to remember, because it’s been like three years ago, but we couldn’t access the storage locker because the elevator got jammed. So we couldn’t take the elevator to the second or third floor, which is where our storage locker was.

I’m outside scoping out the fire exit. I’m like, “Can I scale the fire exit?” You can’t make this stuff up! You could get up the fire exit, and there was a fire door, but there was no doorknob on the outside of the door. I’m like, “Who approved this building?” If this building was on fire, the fire department literally cannot get in because they’re not going to use the elevator, and there’s no handle! How is there no handle on the door?

So I just very nicely said, “You’ve got to get a locksmith, or Jennifer might be breaking a window.”

They’re like, “Well, just come back tomorrow.”

And I’m like, “I can’t! I have 150 people coming in tomorrow, and they need all the stuff that’s up there!”

Crazy. You can’t plan for that. Long story short, they did get a locksmith to come in and let us in a different place. We had to manually walk up the steps because the elevator was still broken, and all the things. It all worked out well, but that was three hours of pure terror. How do you have an event when you don’t… all your stuff, your workbooks, your sponsors… everything was in the storage locker. It was awful.

John SmallMtn (00:43:45)

It was so funny because I ran into you in the lobby of the hotel. I had just checked in, I was about to go upstairs to my room, and I saw you. I was like, “Hey, I’m just so excited to be here.”

The thing that sticks out the most is that even in the middle of all that going on, you were still cracking jokes. You were moving, you had some urgency to you, but you weren’t “woe is me.” You still very much had this attitude of, “Hey, we’re going to get through this, we’re going to figure it out.” Is that easy for you to do, or is that something you have gotten better at by just carrying the stress and walking the path?

Jennifer Bleam (00:44:17)

The show must go on. It’s pretty easy for me. I’ve got three boys and a husband. Now they’re older, and most of them are in college or moving out, but when they were younger, it was chaos. You’re going to soccer and basketball, and you’re like, “Shoot, we don’t have enough drivers.” For a while it was like, “Well, I’m sorry, we only have two drivers and three children, all of whom want to go in different directions. The math doesn’t math, right?”

So, just rolling with the punches is kind of my life. My husband and I laugh all the time, because if we’re hiring a contractor to come in and replace our roof or replace a floor, we’re like, “We just want to warn you: we are the couple that something is going to go wrong with.”

They’re like, “Don’t say that!”

And we’re like, “No, no, it happens every time.”

And they’re like, “What?”

We’re like, “Yeah, it just is.”

And they’re like, “Why?”

We’re like, “We don’t know, but we just laugh.”

Then we make a phone call. We got our roof replaced, and two months later it was raining in our living room. Whatever! We’re like, “It just happens.” Stuff just happens, and it’s out of your control. You could get all bent out of shape, but it doesn’t really help.

John SmallMtn (00:45:48)

Yeah, I have to remind myself of that, because I get very bent out of shape pretty easily.

Switching gears, I want to ask you some of my rapid-fire questions. When someone is going out as a freelancer, solopreneur, or they have visions of being a founder and growing something bigger, what do they need to be thinking about on day one when it comes to AI specifically?

Jennifer Bleam (00:46:16)

I think it’s easier for someone who doesn’t have any processes to put AI in place early, because it’s harder to retool processes and flex AI in. But my caution would be: you don’t want to automate or make something more efficient if it’s broken. I know that sounds so silly, but make sure you have a functional process first before you make it automated. Otherwise, you’re just going to spend a lot of money automating things that are broken. That doesn’t do any good.

Whether you’re creating a flowchart on a whiteboard, Canva, Miro, Post-it notes, or whatever, have an idea what that process looks like manually, so that becomes your specs: “It has to be able to do these things.” Now you’re evaluating the AI solutions from, “Can it do the things I want it to do?” Have an idea what your process is first.

John SmallMtn (00:47:16)

I love that idea that it’s easier to start from scratch than it is to try to come in and meaningfully insert in certain areas. I never really thought about it like that, but we have blind spots, right? “I’m really good at this, and maybe you’re not really good at it, but you just get personal value out of doing those things.”

Zooming in just a little bit to that question, if we could: because a lot of your focus is on sales and growth, specifically in the IT space, how can someone in their first day or first week use AI to help build some momentum, get some things going, and build some pipeline? What is something you would recommend them doing day one, month one?

Jennifer Bleam (00:48:02)

Okay, so there’s a couple. Number one is learn to use AI as a thought partner. Be cautious, because AI is trained to tell you you’re brilliant, so you have to tune it to be like, “I don’t need you to tell me every one of my ideas is good. Every one of my ideas is not good.” You have to be careful.

Especially if you process verbally, use AI to process verbally. I almost used up my maximum number of voice credits on ChatGPT last month, and I’m on the Teams plan. I have a pretty good amount of data there, because I talk to ChatGPT a lot. Claude has the same thing. So, if you process verbally, use AI to just talk things out. Sometimes you’ll find the solution and you don’t need AI; you just need it to listen to you. That’s one thing.

The other thing—and this is something that I build for people, this is not a pitch—if you’re savvy, build an AI board of directors. Just figure out: if you could talk to any three or four brilliant people who have existed in any amount of time ever (because they don’t still have to be alive, there just has to be a body of work), how do they think about things? How do they reason?

Build an AI board of directors, because then you can go to that board and train them on your current offers, your current bottlenecks, your vision, and your goals. Pretend Sam Altman is on my board, and he’s harsh—which is part of why I picked him. To your point, John, founders don’t always have a lot of people to tell them that they’re getting off track, losing the thread, or “Don’t do that, that’s really dumb, that’s not going to move the needle at all.” I need AI people to tell me that. Building an AI board of directors is a great lever to pull.

John SmallMtn (00:49:43)

I love that. I talk about this for mentorship: I don’t care who the person is, they don’t have all the answers for everything that you’re going through, because we’re all a little bit different. That’s where you need to have multiple mentors so that you can put people in the right lanes, listen to them, and then you’re not taking bad advice from people or second-guessing advice that doesn’t make sense (which waters down your trust in that person who has really great advice in other lanes). Don’t put people in bad spots so that they disappoint you. I love that idea.

When everyone has advice, social media makes it really easy to put a lot of advice out there. What is a piece of advice that you can now understand and respect, but you had to learn the hard way by running into the brick wall yourself?

Jennifer Bleam (00:50:35)

There’s this concept called Profit First. Mike Michalowicz wrote this book, and it is simply, instead of saying “Income – Expenses = Profit,” which is our typical accounting way of looking at things, we do profit first. It’s like: Income – Profit = Expenses. We store away the profit, and now we only have X amount to spend.

I’ve only been doing this for six months or so, because I had to learn this the hard way. You hear advice and you’re like, “I’m too small,” “I don’t make enough money,” “Yeah, but…” all the things, right?

It is amazing, because one of the tenets is that once a quarter, you take half of that profit and you pay yourself a bonus. It’s all math, and AI can help you do it. It puts guardrails on your expenses, first of all, which is always good because there’s always something to spend money on. Having that cap, like, “I can’t spend more than X,” means that Facebook ad that I saw, that tool, or the AI solution, I can’t buy that until I increase my revenue. Now we’ve got that external pressure to grow revenue, which is good.

Then, once a quarter, to be able to take an owner’s bonus because of how much your business grew is so empowering. I talk to many business owners that just don’t pay themselves, and it’s demoralizing. We just use algebra to flip the equation around, but there’s something powerful about it. It’s simple.

To your point of taking and tweaking it: Profit First would say have six different bank accounts. I don’t; I have one extra bank account, and profit goes in there. I take all the things that are supposed to go into six different bank accounts and put them into one, and then my accountant does a general ledger sheet to track it all. But the concept is 100% valid.

John SmallMtn (00:52:58)

Yeah, super solid book. I recommend it to lots of people, because just the concept of… when your plate is huge, you’re probably going to overserve yourself. As soon as I read that, I was like, “Ooh, I have some room to improve on this thing.”

Growing up as an ’80s kid—Clean Your Plate Club—and then being in the military where you don’t know when you’re going to eat again, so you make the most of it now… just that concept of making the plate smaller. If you’re running around with all of your money in one account or whatever, you’re probably not being all that discerning with your spending, and it leads to concern, frustration, and anxiety. Phenomenal book.

So, you’ve been in the space for a while and you’ve been walking your path for a while. Independent of business type, what is your advice for someone who’s going to go off and start today?

Jennifer Bleam (00:54:01)

Have more conversations.

Like, “I’ve got this crazy idea, can I run it past you?” It’s not necessarily a sales conversation—it might become a sales conversation—but imagine if you had 20, 30, or 40 of those types of conversations a month! Pure gold.

We can do it on Zoom, record it, and feed the transcripts into AI, and AI can pattern match for us—all the things, right? But you’re going to build your network, you’re going to get great feedback, and it doesn’t even have to be around the offer that you’re creating. It could be: “What are you hearing in the industry? What are people concerned about? Is this a bleeding-neck problem that I’m trying to solve, or is this something where people are going to be like, ‘That’s a nice-to-have’?” That’s not a great model, because people pay for bleeding-neck problems. If it’s just a nice-to-have, when they start to do Profit First, the first thing to go is that nice-to-have thing that is too expensive.

Have those conversations. You’re also building the rejection muscle. Everyone’s not going to agree to have a conversation with you, and that’s okay, because when you’re in the sales seat as the founder, everyone’s not going to agree to buy from you. Everyone’s not going to want your lead magnet. Not everyone is going to say yes. Just have more conversations. The ability to have conversations with people will then dovetail into your sales calls as well. You’ll be able to talk to them.

John SmallMtn (00:55:22)

100%. It’s always my first question: “John, I want to go launch this business.”

“Okay, cool. I’m excited for you. How many people have you talked to about it?”

“Well, none. I just know it’s going to work.”

“Okay, how do you know?”

One of the things that is super important is that, to your point, it doesn’t have to be polished. As a matter of fact, it’s better when it’s not: “I just had this crazy idea.” “Oh, I would never pay for that unless it had this!” Then, when you can capture those stories and use those stories: “Hey, I was talking with Jennifer and here’s what she said. I’m curious, is that relevant to you?” We’re not even having to sell anything.

People who are trying to hire people like you and me have missed this boat entirely, and they’re still running around thinking that everyone should just be buying. “Just shut up and buy! Well, I need sales training.” Okay, well, probably, maybe… but maybe you should have started with a better understanding of what people would be excited to buy, and then you’re not trying to Grant Cardone and shove it down everyone’s throat. Huge nugget.

Jennifer, I want to thank you so much for coming on here. I think there’s a bunch of stuff in here that’s going to help other founders. If people want to keep up with you and learn more about what you’re doing, or maybe they want to come talk to you about an AI board of directors, where is the best place for them to hang out with you and keep up to date?

Jennifer Bleam (00:56:56)

I’m active on LinkedIn—that’s probably the easiest. If you go out to my website, MSPSalesRevolution.com, I’m reachable on there as well.

John SmallMtn (00:57:06)

Awesome. Thank you so much for doing this. I know you’re a little under the weather, but I really appreciate you coming on anyway. That was a cool conversation, and I think it’s really going to help some people. Cheers! Have a great day.

Jennifer Bleam (00:57:16)

Awesome, appreciate you having me on. You too.