- #22 What People Trust Before They Buy
Reputation is one of those things we like to think we control, but the truth is a little messier than that. It is shaped in the moments people remember, repeat, and quietly use to decide whether they trust us enough to work with us or send someone else our way.
This conversation is about more than the usual “referral talk.” It is really about trust, character, experience, and the small behaviors that make someone feel confident putting their own name next to yours.
If you are growing, pivoting, or stepping into a more visible role in your business, this one is worth sitting with because what people say when you are not in the room may be your strongest sales asset, or it may be showing you where the next layer of leadership needs to happen.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
35m - Aug 18, 2026 - #21 When Your Brain Waves the White Flag
There is a point where life stress and business pressure stop politely taking turns. They collide, they pile up, and suddenly the things you usually handle without thinking start feeling heavier than they should.
This conversation is about that founder-level moment when the issue may not be your strategy, your discipline, or your ambition. It may be that your capacity is maxed out, and your brain is asking for support before it turns every decision into a much bigger problem.
If you have ever looked at your calendar, your family, your inbox, or your to-do list and thought, “I cannot keep doing it like this,” this one will feel familiar. Not because it fixes the hard season, but because it names what is happening underneath it.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
32m - Aug 11, 2026 - #20 Finding the Price That Fits
Pricing gets uncomfortable when the number on the invoice no longer matches the version of the offer you are actually delivering. What used to feel generous can quietly turn into resentment, especially when the scope, support, experience, or transformation has grown but the price stayed behind.
This conversation is about the tension between charging with integrity and holding a price that no longer fits. There is a real difference between overdelivering because you care and overdelivering because your boundaries, confidence, or offer structure have not caught up yet.
If you have ever wondered whether your price needs to go up, your offer needs to get stronger, or your client relationships need cleaner expectations, this one will feel familiar. It is a grounded conversation about value, maturity, and learning to say the number without spiraling afterward.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
34m - Aug 4, 2026 - #19 The View You Can’t Get Alone
There is a strange kind of frustration that shows up when you are great at seeing the next move for everyone else, but your own business feels harder to sort. When everything has history, context, pressure, and possibility attached to it, it gets harder to tell the difference between what’s working, what’s not, and what you need to just wait out.
If you are in a season of business where your brain feels tangled trying to hold it all, this episode will feel familiar. It is a coffee-fueled reminder that needing outside perspective does not make you less capable. It may be the thing that helps you lead with a little more clarity.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
32m - Jul 28, 2026 - #18 When Their Success Feels Like a Threat
☕ Grab your favorite caffeinated beverage and join us for today's episode, where we're going behind the brew of issue #68: When Comparison Hijacks Your Brain
Comparison gets weird fast when someone else’s win starts feeling like a threat. It is one thing to notice success and feel inspired by it. It is another thing entirely when your brain starts building a whole story around why someone else got what you wanted faster, easier, or louder than you did.
This conversation is about the less polished side of comparison - the part where jealousy, frustration, and public reactions can start shaping how people experience your brand. Because the way we handle someone else’s success says a lot, especially when we are still building our own.
If you have ever felt that sting when another founder seems to be winning faster, this one will feel familiar. We are talking about what happens when comparison gets loud, how to process it without letting it spill everywhere, and why someone else’s visible success is rarely the whole story.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
30m - Jul 21, 2026 - #17 When Success Stops Looking Like a Number
There is a strange thing that happens when you spend years chasing business goals. You can hit the number, book the client, cross the milestone, and still feel like you are waiting for success to finally arrive.
This conversation sits in that uncomfortable space between achieving something you’ve been working towards and actually feeling the thing you thought achievement would give you. Because sometimes the evidence that the business is working does not show up as a dramatic win or big milestone. Sometimes it shows up in a very normal moment that suddenly feels like a reason to celebrate.
If success has ever felt harder to recognize than achievement, this one is for you. It is a conversation about ambition, perspective, and learning to notice the ordinary moments all your work is making possible.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
28m - Jul 14, 2026 - #16 When Help Turns Into Rescue
If you’ve ever left a client situation feeling guilty, this episode will feel uncomfortably familiar. There’s a difference between guiding someone through the work and quietly taking responsibility for results they aren’t fully owning.
Bernie and I talk about how this shows up in real life with clients: expectations that were never truly aligned, the “easy button” energy that sneaks into the room, and the moment you realize you’re trying to want someone’s success more than they do.
This one is for the service provider who wants to help people win, but wants to do it without becoming the hero of someone else’s story.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
28m - Jul 7, 2026 - #15 The Thin Line Between Your Vision and the Danger Zone
There’s a kind of belief you need in business that looks a little unhinged from the outside. Not because you’re reckless, but because you’re willing to move before you have proof, and you’re willing to be misunderstood while you do it.
In this episode, Bernie and I talk about that line founders cross without realizing it, the moment vision stops being leadership and starts turning into obsession, overreach, or the danger zone. We also get honest about how much your environment and inner circle can either steady you… or quietly push you into decisions you’ll have to clean up later.
This one’s for the established entrepreneur who’s building something bigger than what their current season can comfortably hold, and wants to stay ambitious without losing integrity, relationships, or sanity.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
31m - Jun 30, 2026 - #14 The Reps That Build Real Momentum
If you’ve been stuck in a loop of “I know what I should do… I’m just not doing it,” this is your permission slip to stop making it dramatic. In this episode, Bernie and I talk about the 30-day challenge mentality: picking one uncomfortable action and doing it daily long enough to build the habit and strengthen the muscle.
We get into why the first week feels clunky, why your brain starts negotiating around day 10, and why the reps matter more than the mood. Because by the time you hit week four, you’re not just “doing the thing,” you’re better at it, calmer doing it, and you’ve built real momentum you can actually ride.
And Bernie and I both declare our own personal 30 Day Challenges to each other (and you are welcome to be a part of it!)
If you want a founder-level reset that isn’t a total reinvention, this is it. One decision. One daily rep. Thirty days. And a very real chance you’ll surprise yourself with what happens when you stay in it.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
27m - Jun 23, 2026 - #13 The Loneliest Part of Business
Entrepreneurship can feel like you’re building something important while the street stays weirdly empty, no water cooler, no built-in coworkers, and not always a clear place to put the hard stuff (or the good stuff) when it happens.
In this episode, Bernie and I talk about what that loneliness actually looks like in “real life business” and the difference between needing someone for the tough days versus the wins you’re scared to say out loud, the way we each spiral (or shut down) when it’s an “empty parade” season, and why oversharing with the wrong people can cost you more than staying quiet.
We also get practical about the kind of support that actually helps from your “Core 4” and how a relationship-first networking culture can quietly become the bench you lean on when you need perspective, encouragement, or someone to talk you off the ledge.
If you’ve ever felt like your “parade crowd” looked more like an empty street, this one’s for you!
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
31m - Jun 16, 2026 - #12 When “Just Ask” Changes Everything
You can work hard, show up consistently, and still feel like your audience is just… watching. This episode is for the moments when you’re doing “all the things” but sales feel oddly quiet, and you can’t tell if it’s your offer, your messaging, or something you’re missing entirely.
Bernie and I talk about the kind of market research that actually matters…the kind that tells you what people want in their own words, not what you hope they want. Because it’s a whole lot easier to sell someone something they already want than to convince them they should want what you built.
If you’ve been posting and praying and calling it strategy, consider this your nudge to stop guessing and start asking. This is founder-level, real-life clarity for anyone who’s ready to get out of the “create and hope” cycle without reinventing their entire business.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
32m - Jun 9, 2026 - #11 What Your Kids Learn From Your Business (good or bad)
This episode is really about the part nobody talks about: your kids are learning business from you whether you’re trying to teach them or not. They’re watching what success does to you, what failure does to you, and what you make it mean and they’re quietly building their own beliefs about work, risk, money, and resilience from the way you handle it.
Bernie and I talk about the difference between what we say we value (boundaries, family, staying steady) and what we accidentally model when the pressure hits (when the launch flops, when the cash feels tight, when you’re winning but still living like you’re behind). Because your kids don’t take your advice. They copy your actions.
If you’ve ever wondered whether you’re passing down grit… or anxiety… or a workaholic badge of honor… you’ll hear yourself in this one. It’s a coffee chat about succeeding, failing, and recovering out loud, so the people watching you learn the right lessons.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E11 - 40m - Jun 2, 2026 - #10 The Gap Between Good Advice and Real Results
Most of us aren't stuck because we lack access to good advice. We're stuck because we treat someone else's strategy like a buffet, taking what looks good, skipping what's uncomfortable, and then wonder why it's not working like promised.
In this episode, Bernie and I get honest about what actually has to happen for advice to move from "that's so good" to actually changing how you operate and we are honest about the gap between consuming content and implementing it, why good intentions aren't the problem, and what it really means to surrender to an approach versus just going through the motions.
If you've ever taken a course, had a great coaching call, or bookmarked a podcast and done absolutely nothing with it (my hand is raised!!)…this one's for you.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E10 - 30m - May 12, 2026 - #9 Stop Chasing: “Follow-Up” Shouldn’t Look Desperate
If you’ve ever stared at an open email thread and thought, “Okay, is this quality follow up, or did I just turn into a teenie bopper waiting on a text back from their crush?”… this one’s for you. We talk about the moment a warm lead turns weird, and how fast your confidence can leak out when you start trying to interpret someone’s silence instead of responding to it.
In this episode, Bernie and I get honest about where that line actually is between professional persistence and straight-up chasing. We unpack the subtle signals people give (and the ones they don’t), what it looks like to close the loop without burning the bridge, and why “fortune is in the follow-up” doesn’t mean you need to keep knocking on a door that’s clearly not opening.
You’ll walk away with a clearer gut-check for your next follow-up, a better way to stay in your CEO energy when someone’s dragging their feet, and a little permission to stop making excuses for prospects who won’t decide.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E9 - 28m - May 4, 2026 - #8 When the Detour Becomes the Main Route
Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #19: When “Under Construction” is an Understatement
What does it actually looks like when your business is “under construction” for real? Not just a cute rebrand season, but the kind where the platform shifts under your feet and the systems you built on suddenly stop cooperating.
In this episode, Bernie and I get into the very specific pain of rebuilding while you’re still delivering, still selling, still trying to act like you’re totally fine… while your brain is quietly running a demolition crew in the background.
We also pull apart that tricky question: is this broken, or is this just growth? And what do you hang onto as non-negotiable so you don’t rebuild the wrong thing.
And yes, we’ve both had a moments where we discovered “if the detour is better, you have to make that the main route” which is annoyingly true, but also kind of relieving if you’re in a season where the best next step isn’t the one you planned.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E8 - 31m - Apr 28, 2026 - #7 When Opportunities Start Punching Back
☕ Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #16: Opportunity —> Problem —> Repeat
I laughed when I pulled this issue from the archive because it’s one of those “oh cool, we’re doing this again” themes and apparently my business heard me and said, “Bet.”
Bernie and I swap stories on the funniest “opportunities turned problems” experiences (someone offered to book me private jets…I don’t think my LinkedIn profile makes me look that successful!), and we talk about what to do when people interrupt your day with a cold pitch. I tend to Uno-reverse them, but Bernie has a mischievous approach, of course.
Then we get into the less-funny part of growth: when the role that helped you build the business isn’t the role you need now and we wrap by normalizing the cycle: bigger problems usually mean you’re playing a bigger game, but repeating the same problems might mean you’re the problem you keep having!
Give it a listen and if you’re in the trenches, fighting business battles right now too, just know you’re not alone… we’re in it with you!
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E7 - 25m - Apr 21, 2026 - #6: When Momentum Becomes a Distraction
☕ Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #43: Why Your Word of the Year Is Lying to You
I’m not anti–Word of the Year… I’m just very familiar with the moment you look up and realize you ghosted yours by February without even noticing. Mine was “Focus,” and the funny part is, I didn’t rebel against it. I just got busy and called it momentum.
Bernie and I talk about shiny-object season and why it’s almost impossible to label something as a “distraction” in real time (especially when the opportunity is genuinely good). We also get honest about how quickly “fun” collaborations can start quietly hijacking the commitments you swore were non-negotiable.
By the end, the question isn’t “Should I try harder?” It’s “Is this a recommit moment or a release moment?” And if you’re not regularly asking what’s working and what isn’t, you’re basically outsourcing your year to whatever shows up loudest.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🌐 http://www.leadsmarterco.com
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E6 - 25m - Apr 14, 2026 - #5 Does Your Boss Owe You a Raise? (oh wait...that's YOU!)
☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #5: I Made More Money and Still Felt Broke (Here’s What I Missed)
In this episode, Bernie and I talk about that maddening moment when your business is ‘doing well’ on paper… but your bank account still hasn’t gotten the memo.
We get real about the stuff that quietly drains you, like subscriptions you forgot you had, upgrades that felt “responsible,” and reinvesting so hard you never actually feel the win. We also share a couple of our own stories (credit cards, bad timing, and yes, me being annoyed that Bernie’s audio is better than mine).
Then I walk through my CEO Expense Checklist, because at some point you have to ask the question nobody wants to ask: is this decision building a business that takes care of you, or just a business that keeps taking.
If you’ve ever hit a revenue milestone and still wondered where the money went… then this one is for you.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E5 - 27m - Apr 7, 2026 - #4 Sometimes Your Brand Choose YOU
☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #25: The Cat Poop Coffee of Branding
Okay, real question: would you drink the cat poop coffee… and what would it take for you to say yes?
That’s where we start today’s conversation, but what it turns into is the kind of honesty you usually only get from entrepreneurs deep in the trenches of building their brands.
If you’ve ever felt like your work is solid but you’re still blending into the noise, we talk about why “good” isn’t memorable, and why playing it safe is usually the problem. We walk the line between what is authentic vs. gimmicky, and what it feels like when you intentionally stop trying to be universally liked.
Plus, the touching origin of Mustache Moments and the story about the eyelash that abandoned ship mid-zoom call give you a peek behind the curtain of how we developed our own signature brands… because sometimes you don’t choose your brand, it chooses you! Tune in, you’ll probably have an opinion on this one.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E4 - 27m - Mar 31, 2026 - #3 Letting Go So You Can Grow Again
☕ Grab your favorite caffeinated beverage and join us for today's episode where we're going behind the brew of issue #42: Why You’re Not Making More Money (Even Though You’re Brilliant)
Bernie bought a business. Or at least he thought he did. Turns out, what he really bought was a name and a handful of relationships that weren’t fully his yet.
In this episode, we talk about what it felt like to have a million-dollar year… and then watch major clients disappear. About holding onto an old model longer than you probably should. And about that moment where you realize the thing that used to work isn’t what’s going to carry you forward.
This isn’t a “here’s how to pivot” episode. It’s just an honest conversation about what it looks like to loosen your grip, stop splitting your focus, and finally commit to the direction that’s actually gaining traction.
If you’ve ever known something needed to change, but weren’t quite ready to let it go, this one will probably feel familiar.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
S1E3 - 20m - Mar 24, 2026
