
The Art Of Entrepreneurship · 2026-06-30 · 19 min
Key moments - from our scoring
Substance score
34 / 100
Five dimensions, 20 points each
Founder and CEO Jackie Hermes unpacks the critical but often-avoided topic of reinventing your role as your business grows beyond its startup phase. Drawing from her 13-year journey building Accelity from zero to seven figures, she distinguishes between proactive reinvention (driven by restlessness and readiness for new challenges) and forced reinvention (when the business outgrows your current operating style). Hermes shares humbling lessons: early micromanagement that capped company potential, a painful over-correction where she stepped back too aggressively and lost deals because clients wanted founder involvement, and her current proactive pivot toward AI-forward marketing to keep the agency competitive. She emphasizes that reinvention isn't disengagement - it's recalibrating involvement. Her framework includes auditing where you're truly needed versus comfortable, matching your exit pace to team readiness, letting team members own both wins and failures, and rebuilding your role around high-leverage activities aligned with business needs. The episode speaks directly to founder bottlenecks and the trap of staying comfortable in outdated roles.
Proactive signals include restlessness, boredom, not learning, and a calendar full of things you should say no to. Forced signals include becoming a bottleneck, dropping balls, things overflowing your plate, and the business moving faster than you are. Both mean your current role has expired.
Reinvention requires staying engaged and involved at an appropriate level; checking out is disengaging, taking sabbaticals, and stopping showing up. Founders who confuse the two often wonder why things fall apart or drift.
Audit where you're genuinely needed versus where you're comfortable, train people clearly before handing things off, establish solid processes and feedback loops, and involve yourself in high-leverage activities and strategic decisions - not every problem.
Listen to the feedback, recognize it's right even if it stings, apologize if needed, and recalibrate - match the pace of your exit to the team's actual readiness and the business's stage, not to theory about what leaders should do.
Empower them to own both wins and failures, don't parachute in for every problem, guide them through challenges they solve themselves, keep them challenged but not so comfortable they get bored, and recognize when reinvention means they may leave - that's often a sign of a healthy culture.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode offers a handful of useful observations about founder role evolution - particularly the overcorrection danger of exiting too fast - but the bulk is familiar entrepreneurship wisdom (micromanagement early, delegation as survival, work on vs. in the business) padded with personal narrative. Insight-per-minute density is low for a 19-minute runtime.
comfort is how founders become the thing that are holding companies back. And nobody tells you because you're the boss
match the pace of your exit of these certain roles to the readiness of the business
The most genuinely original moment is the overcorrection story - pulling back too fast and losing client deals because the founder disappeared from the sales process - which is an underexplored failure mode. Everything else (adapt or die, delegate or drown, work on not in the business) is explicitly drawn from or mirrors well-worn frameworks.
we lost deals because people were like, at this size of the business, I do want to see the founder at least in the sales process
I definitely tried to grow myself out of the business too fast
This is a solo episode; there is no guest. The host is a genuine 13-year agency practitioner who built to seven figures without funding, which gives her earned credibility, but the episode is limited to a single practitioner perspective with no external expertise or tension.
I grew my company acceledy from zero to seven figures with no partners and no funding
I'm 13 years into excelity and I've definitely had periods of time where I'm like, what am I still doing?
Concrete evidence is almost entirely absent: no revenue figures, no client names, no team size milestones, and no AI tool specifics despite the AI pivot being a central claim. The only quantifiers are vague timeline estimates and episode numbers, leaving all anecdotes at a frustratingly abstract level.
we lost Some deals and some clients. And it stung
This was probably, I don't know, maybe eight, eight years ago at this point
This is an uninterrupted solo monologue with no interviewer, no follow-up questions, and no productive tension. The episode does have a coherent five-step framework delivered at the end, but without a guest to challenge or probe, the craft ceiling is structurally low and the host does not challenge her own claims with any rigour.
So if you're trying to figure out how to reinvent your role, or I guess, whether it's even time to reinvent your role, how I would think about it is as follows
All right, y', all, it's shameless. Plug time.
Computed from the transcript - who did the talking, and the words that came up most.
This episode of The Art of Entrepreneurship is for founders realizing reinvention means becoming the version of themselves their business needs next. A few episodes ago, I talked about the long middle of entrepreneurship and how staying in that phase is about more than endurance. It’s about figuring out how to keep growing inside the company you already created. This episode is the other half of that conversation. Because as your business grows, your role has to change with it. I talk about the difference between proactively reinventing your role and being forced into it because the company has already outgrown how you operate. I also get into what reinvention is and what it isn’t, including why stepping back too fast can create just as many problems as holding on too long. Reinvention doesn’t mean checking out of the business. It means becoming more intentional about where you’re involved, where your team is ready to own more and where your involvement creates the most leverage. The biggest shift is learning to tell the difference between being needed and being comfortable.
Transcribed and scored by The B2B Podcast Index.
Speaker A: We're not one of those agencies that wakes up one day and people don't want to pay for our services because they are too manual and other agencies have adapted. I do think that you have to adapt or die as a marketing agency and we are not going to be one of the ones that's died. Building a company from nothing is freaking hard. Us, uh, entrepreneurs are expected to deal with unimaginable challenges and somehow keep a cool head through it all. This is the Art of Entrepreneurship and I'm your host, Jackie Hermes. I grew my company acceledy from zero to seven figures with no partners and no funding. The Art of Entrepreneurship is a show where we cut through the BS and dig into what it actually takes to start and grow a company. If you give me your time, I promise it won't be wasted. Now let's get to work. Hello and welcome back to the Art of Entrepreneurship. So a few episodes back, well, probably a few months now, in episode 318, the last long Middle of Entrepreneurship, I ended by saying that I was going to expand in my next solo on a topic, and then I didn't. So I'm going to do that now. So if you haven't listened to that episode, it might be a good time to go back and do that before you listen here. So in that episode I talked about how you have to keep growing and kind of reinventing yourself in a company that you already created if you want to stay just interested and excited or you kind of have to move on. Honestly, like, I'm 13 years into excelity and I've definitely had periods of time where I'm like, what am I still doing? It's like a, um, a long job that you didn't know you were going to have for this long. So you have to reinvent your role proactively and honestly. Sometimes you don't get to do it proactively. Sometimes you're kind of forced into it because things get stuck, stale, or because you're not growing as fast as you should be or as fast as a business demands. I've been through both where I do it proactively because I want to, and I'm all motivated about it, and then I've been forced into it. And I'll talk about both today. I think when you do it proactively, it is that decision. You see a next stage of the business coming and you get to start, like plotting change and planning for the future. Forced reinvention feels hard. It's like rolling a boulder up a hill when the company has already outgrown the way that you yourself are operating, and you're the last one to find out. It's not cool and it's not fun. Neither one really means that you're failing, but one situation is more comfortable than the other. Not that either is really comfortable, but let me be very clear, that neither is about checking out. Like, you can't check out any time during this process. I think some founders hear reinventing your role, and what they actually do is disengage. They're like, I need to take a sabbatical, and I need to rethink everything that I do, what I need to do to rethink my role. I need a vacation. I need time. And then they stop showing up, and they're like, I'm delegating and I'm, um, leveling up. And then they wonder why things fall apart or things drift. That's not reinventing. That's like abandoning your responsibilities. Today we're going to talk about redesigning your role while staying engaged, because that's what your business needs ultimately, is you as a leader to stay engaged over time. So I was trying to think back as I was prepping for this to, like, when. When were all of the times that I reinvented or I was forced to reinvent? And I think one of the earliest times was early on when I micromanaged. I really wanted the business to be a reflection of me and the way that I do things. And I think that's probably a very common trap that you fall into when you create a business that's based on your own skills. And when a company is young, you are the business. I talked about this in episode 308. Every deliverable, every client interaction, every email has your name on it pretty much. I mean, it didn't, but it kind of did. The thing about building a company that is like every. In every way a reflection of you, it can only ever be as good as you. And there are so many people that are better than you at things. When you build a company like that, you're kind of like, capping it. You're capping it by your skills, your energy, and your blind spots. Because even if you're one of those people that think you're good at everything, you're really not. It's not. What I know now as a leader that I didn't know a decade ago is that people around me are way better at a lot of things. And you have to accept that early on, and it should be true. Like, if you're the best person in the room at everything. You're not aiming high enough and you're not surrounding yourself by the right people. So at that time, I kind of got forced to, to build better around me. My job stopped being make every process the way that I wanted it. And it became let the people around me grow areas of the business with my guidance and my feedback and guardrails instead of having like, my fingerprints, my little hands and everything, those are completely different things. And honestly, I have met leaders even today that still don't understand that. And I think that really frustrates people on their team. That was a season when I got so full and so busy that delegation wasn't a philosophy. I didn't learn to delegate because I was like, ooh, I'm gonna delegate. It was like survival. When your plate gets so full that you have to delegate because you're overflowing and you don't gracefully hand things off. You slap things on other people's plates and then you annoy them because they don't really know what's going on. Because you didn't delegate well. You didn't train people, you didn't explain what you'd be doing. But I mean, that can be a legitimate way that reinvention happens. But it was messy and it was not great. There was definitely some turnover during that time, some hard conversations, and I had to open my eyes to a better way to proactively reinvent. There's another part of this story that I want to share because, I don't know, I think leaders probably do this, but I've never heard anyone else talk about it. At one point, I definitely tried to grow myself out of the business too fast. This was probably, I don't know, maybe eight, eight years ago at this point. I think I'd taken, uh, in all of the advice that I needed to work on the business and not in the business, that I needed to fire myself from the day to day operations of the business. And I needed to get out of the way. And so I pulled way back and I put managers in place. And it just didn't work the way that I wanted it to because I was too uninvolved. Like, we lost deals because people were like, at this size of the business, I do want to see the founder at least in the sales process, or I at least want to see them at the strategy pitch.
Speaker B: Right?
Speaker A: Like, you can't just totally disappear and be uninvolved. And I got that feedback from, from my team and from clients, and we lost Some deals and some clients. And it stung. And I was defensive because in my head I thought I was doing the right thing. But in hindsight, I ended up having to go back and apologize to some people because I was like, oof, this is a very humbling experience. And that feedback is right. And sometimes you get the most defensive about feedback when it is spot on and you know it's right. Reinvention isn't always about you being ready and willing to change, but it's about the business needing a new version of you from you. And those are really different things. Right now we're also in a phase of reinvention, and that has been a shift toward AI and that has been a much more proactive reinvention. That has been exciting, it's been exploratory. It's been me diving back into work because I want to and because I want to be ahead of the game. Right. And I want to ensure that our company is an AI forward marketing agency so that we can stay relevant and that we can build our processes using AI and that we're not left behind. And we're not one of those agencies that wakes up one day and people don't want to pay for our services because they are too manual. And other agencies have adopted. I do think that you have to adapt or die as a marketing agency agency and we are not going to be one of the ones that's died. All right, y', all, it's shameless. Plug time.
Speaker B: I want to take a quick break to chat with you about Excelity, my full service marketing agency. For the last 12 years, we've been working closely with B2B software and service companies. Now we are expanding and looking for growth stage companies with a, uh, bold vision, but maybe lacking the marketing strategy or resources to get there. Or, hey, you might have resources that just aren't working out. We definitely see that all the time at Accelity. Our team gets results and we have a ton of fun doing it. I'm sure you can tell that from listening to this podcast. So if you or someone you know is a fit, check us out@excelitymarketing.com or reach out to me directly on LinkedIn.
Speaker A: So this is one where I have gotten to proactively reinvent and proactively learn. And it has been a lot less painful than the other two situations that, you know, that I just described. Now, 13 years in, my role has gotten much more advisory. Like, I do way less of the client work, but it has grown in a natural way where my Team truly holds client relationships. And I don't hover over them all the time. And I do a lot more of, I guess what my business coach used to call shaking hands and kissing babies. So I hold a lot of our important relationships. I check in with clients, um, but I get involved where I want to be in the strategic, important, high level things. I don't even have to deal with every problem anymore. And that is fantastic. That is what Jackie of eight years ago, that story that we just talked about wanted. But I think she pushed too hard and too early. And what made that possible is empowering the team to own the good and the bad and building that over time. I think that's really powerful. And that's also the hardest part of kind of reinventing your role over and over again. You also have to help other people reinvent themselves over and over again. And that's what a good leader and a good coach does. And you have to realize that sometimes when people are reinventing themselves, they are going to leave. We have really great tenure within the company and I think that is because we not only allow people, but we guide them in reinventing themselves over and over again. They're comfortable, but they're not too comfortable because we do keep them challenged and engaged. We don't want them to be too comfortable where they're bored and they're looking for that new challenge all the time. When it comes to letting your team or getting your team to own the bad things, I think just letting them own the wins is easy. And I think everyone loves taking credit. But letting them or getting them to own the Mrs. And the hard conversations and the problems is a real test. And it's really rewarding when you learn how to do that and uh, when you don't kind of parachute in or pop up for every problem and you don't handle everything for them when they do it, it's really rewarding to come to the end of a challenge and having figured it out yourself and you're able to really strengthen that relationship as well. So if you're trying to figure out how to reinvent your role, or I guess, whether it's even time to reinvent your role, how I would think about it is as follows. First you have to figure out what season you're in. Uh, is it time to reinvent your role? And if so, are you being forced? Is this proactive? Like we said, the signals are different. When it's proactive, it's kind of restlessness. Things might be stable, but you're ready for change or challenge, you're bored. You're not learning. Your calendar is full of things that you should have said no to that don't energize you anymore. When you feel stale, that can be a sign. That can be a signal. When it's forced, that's pressure. You're a bottleneck. Everything is stacked up behind you. You're dropping the ball. Things are overflowing off your plate. The business is moving faster than you are. Both are kind of telling you the same thing. And that is basically your role as it stands today is expired. And I think one is just more comfortable than the other. The second thing that I would do is audit where you are involved in your business and then ask yourself, honestly, am I needed? Am I comfortable? Who can handle this without me? Who can I train up? Are they already handling it without me? And I'm just involving myself because I want to be here. If you're needed, it means a business genuinely requires you there. But comfortable, I don't know. You're familiar. You've been doing it a long time. There's so many people, business owners, that are still doing little piddly things that frankly, you could automate with AI or you could delegate. I think comfort is how founders become the thing that are holding companies back. And nobody tells you because you're the boss. And it's really hard to get feedback when you're the boss. Third, and I think this is a big lesson from my overcorrection story earlier, is match the pace of your exit of these certain roles to the readiness of the business. So don't yank yourself out of something before people are ready. Like, are the processes solid? Have you run through them? Have you gotten feedback on them? Are there good leadership standards in place? Is everyone trained well? Is quality going to hold up when you're not in the room? And then watch for feedback. Gather feedback with people. Do you have feedback loops in place? If you do, then make sure you're listening to people and you're taking that feedback to heart. The goal isn't to be uninvolved or removed. It's to be involved at an appropriate level. And then fourth, make sure you let your team own the good and the bad. We just talked about this. But full ownership is ownership. When they own the wins, they get the credit. And give them credit for all of the wins. Honestly, as leaders, we. We get a lot of wins and we don't need the credit. And let them also take the fall for the bad and let them fix it. That is when they really become strong professionals and future leaders. And then last, make sure that you rebuild your role around what you want and then some. It's not everything you enjoy is what you should be doing. It's everything that you should, you enjoy plus the high leverage activities for your business. So, so for me that's results, it's processes, it's exploring of uh, new. What's new. So new marketing procedures. What should be happening in the world of AI, the world of generating results. For you it might be product or vision or sales. It's going to be different for everyone, but you should be able to name it. And I bet as you're listening, things are coming to mind. So just remember, the version of you that started the company is not the version that runs it forever. And frankly, the version of you that started the company changes probably every couple of years. And if you proactively reinvent yourself in that role every couple of years, you're not going to be dragged along. But you have to look at yourself, your behavior and how you're involved in every part of your company with a critical eye yourself. Because it is so hard to get that feedback as a leader. Otherwise you are going to become that bottleneck. You're going to become the reason people leave. You're going to become the reason that the business fails. So if you wrote your own job description today, not the one that's on paper, but a real job description of what you actually do, does it look different than it did a few years ago? And if the answer is no, then you needed to hear this. Maybe you know someone else that needs to hear this. Make sure you share it. If you have found your perfect role or you have stopped evolving inside of your company, that's not okay. All right, if this one hit home, please share it on social. Send it to one person who needs to hear this message, who needs to get out of every little day to day issue, take a step back, reinvent themselves or a, ah, professional who needs to reinvent themselves inside their company or role. And if you haven't heard episode 318 the Long Middle of Entrepreneurship, make sure you go back and listen because that is the other half of this conversation. And I will see you in the next episode. Sam.
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