Beyond the Balance Sheet: Jen Hamilton’s Quest to Save Small Businesses | Fractional C-Suite Series

How can an entrepreneur build a thriving fractional COO business and empower small businesses to succeed?

In this episode, Jen Hamilton, founder of Hamilton COOs, shares her journey from working in accounting to launching her own fractional COO firm. She discusses the importance of empowering emerging COOs and providing strategic leadership to help small businesses grow.

Jen highlights the value of fractional COO services for companies in the $1-20 million revenue range, helping them build infrastructure and execute strategic plans. She emphasizes focusing on businesses that prioritize serving clients and employees, not just profitability.

As the leader of the Fractional COO Collective, Jen aims to create a supportive community for fractional COOs to learn from each other and overcome challenges. She shares insights on business development, common client mistakes, and strategies for increasing profitability.

Jen discusses overcoming her own fears to launch her business, emphasizing the importance of having a strong support system and accountability partners. She also shares her unique experience as a petite woman practicing Brazilian Jiu-Jitsu, which has helped build her confidence in facing challenges.

Resources and Mentors that inspired Leah:

  •  Darren Hardy – provides valuable business insights and courses
  • “Traction” by Gino Wickman – a classic book for COOs
  • “E-Myth” by Michael E. Gerber – another essential read for COOs
  • “Predictable Success” by Les McKeown – offers valuable business strategies
  • “Simple Numbers” by Greg Crabtree – helps with financial understanding for business owners and COOs

Tune in for valuable insights on building a successful fractional COO business, empowering small businesses, and creating a supportive community for like-minded professionals.




Welcome to another edition of inspired stories where leaders share their experiences so we can learn from their successes, how they’ve overcome adversity, and explore current challenges they’re facing.

Anthony Codispoti (01:23.725)
Welcome to another edition of the Inspired Stories podcast, where leaders share their experiences so we can learn from their successes and be inspired by how they’ve overcome adversity. My name is Anthony Codaspote, and today’s guest is Jen Hamilton, founder of Hamilton COOs, where she serves as both a fractional chief operating officer, or COO, and a mentor for COOs. Her mission is to save and empower small businesses by emphasizing strategic leadership, leading the leaders,

and executing plans with precision. She shares insights on leading with empathy, fostering a culture of accountability, and executing strategic plans that align with the company’s long -term goals. She is also the leader of the Fractional COO Collective, where fractional COOs and integrators can support each other. Now, before we get into all that good stuff, today’s episode is brought to you by my company, Ad Back Benefits Agency, where we offer very specific and unique employee benefits.

that are both great for your team and fiscally optimized for your bottom line. One recent client was able to add over $900 per employee per year in extra cash flow by implementing one of our proprietary programs. Results vary for each company and some organizations may not be eligible. To find out if your company qualifies, contact us today at addbackbenefitsagency .com. Now, back to our guest today, the CEO of Hamilton COOs. Jen, I appreciate you making the time to share your story today.

Jen Hamiltno (02:50.33)
Anthony, thanks so much for having me here. It’s my pleasure.

Anthony Codispoti (02:53.388)
So Jen, tell us in your own words, what does Hamilton’s COOs do and how did you first get started with it?

Jen Hamiltno (03:00.634)
Hamilton COO says two things really. We equip and empower that emerging COO or that existing COO that’s within small businesses or growing businesses. It’s not a, there’s no COO school. Like I had to go learn it through experience and learn it through mentorship. So we offer mentorship training and tools and resources for those who are in those seats. Sometimes it looks like an office manager who’s growing into the COO. Sometimes it’s a full COO in those seats. So.

helping equip them to be their best. And then sometimes there’s companies that don’t have that CEO, but need that second in that command, someone to strategically figure out things with and make decisions from a place of what’s gonna avoid risk, get to those growth areas, hit those goals, that kind of thing, and lead the team, get the team to do their best. And that’s what a CEO’s main job is, is strategizing, getting the team to implement.

to get to those goals. And so if you don’t have that person, then myself or other fractional COOs on my team can also sit in that seat for you, grow you to a point where we can get someone in there full time. And so you get the full gamut of being able to support that seat for the small businesses. Cause it really is difficult when you start a business to know how to run a business. Cause you’re usually coming into it cause you’re a master of your craft.

You’re great at what you do, great at what you produce, but not always great at business. So we come in and fix that.

Anthony Codispoti (04:31.66)
So, would it be the case that a lot of your clients, it’s sort of a short term or a midterm kind of arrangement with you? Because it almost sounds like you’re trying to coach your client to fire you. Right?

Jen Hamiltno (04:47.514)
Yes, it is the goal. A strange goal from a business development point of view, but to me, I’m really about that concept of teaching them to fish, not giving them a fish. And so for me, I am about really having them have the infrastructure and the team that they can rely on. And if I wrap it too closely around me, it’s just the same problem. Right now, before I come in my…

potential clients, they’re wrapped around usually the business owner. And so if I just change that wrap around someone like myself as a fractional CEO, that doesn’t actually really solve it. Because the last thing I want to do is step away and it all crumble. So it’s to me, it’s really much more about leading for the future. Who can start to take over that second and command? Maybe there’s someone internally, maybe there’s someone we need to bring in, but it’s not just the second command. It’s

those that are leading the different functions, the different areas of the business, also strengthening their ability as leaders, as strategists, and as folks who can truly work together. Because those are what they need to do so that the business owner can rely on their team. If it’s only relying on me, that fails.

Anthony Codispoti (06:05.226)
Is there a particular revenue size of client that tends to be a good fit for you? You know, they’re to the point maybe where the founder, the owner is a little bit, you know, in over his or her head, but they haven’t grown to the point where they’ve got that solid internal COO person.

Jen Hamiltno (06:26.618)
It’s a great question because there is a phase in your growth that works and it doesn’t work for having a fractional COO. So having someone come in and actually help you run that business part time, the sweet spot I like to say is about one to 2 million in revenue and it kind of tops out around 20 million. It’s not a perfect science, but the idea is that you have enough income.

that you can support and need to get the things off of your plate of leading your team. You’ve built enough essentially client and revenue and team that you can’t handle it anymore, so you do need someone else. And then it tops out because as you really start to have multiple layers within your company, you’re a bit larger. Now it’s time to bring in a full -time COO. And so it’s that sweet spot in between.

That being said, I do have clients that are under one million and are in that growth stage. That’s where we do a little bit more on the mentoring side, maybe work with someone they have internally that does the execution of the administration of the business and coaching and guiding them and helping them put some pieces in place is a more affordable way than having a full fractional COO. So I do try to work with anyone from say about 500 ,000 all the way up to 20 million because,

They just are struggling with the infrastructure and that’s my focus is how to get the infrastructure of a company to be strong.

Anthony Codispoti (07:58.602)
Now, aside from the revenue parameters that are kind of loose, not up in a hard and fast rule, what are some other criteria that makes a good fit for you in a client? Are there particular industries or particular types of people or leaders?

Jen Hamiltno (08:13.114)
For me in particular, I love working in the professional service field. I started my career as a CPA, I’m still a CPA. I also started my career married to an attorney, I’m still married to an attorney. So I really understand, and then I’ve been in coaching and consulting and fractional leadership. So I understand the high level intellect type of job and how to turn that into a service. So I understand the need for being that trusted advisor.

You know, all of the things that come along with that you have a high level service as your product and your people are your product. So that’s my favorite spot to be in. But I have some qualifications. You have to be a business for good. And what I mean by that is that if you’re out there just for profitability, I’m not your gal. I am going to really lean into how to best serve your clients and how to best serve your…

serve your team because your whole business, especially in professional service, is built on your people. And part of my sweet spot is to have your people be their best and bring their best to your clients. So if that’s not what you’re interested in, then we’re not going to be a good fit for each other.

Anthony Codispoti (09:25.609)
You know, talking about team, and this is something really important, especially in the really tight labor market that we’re in now. I’m curious if you have encouraged your clients to try any strategies that have been particularly effective in recruiting and retaining good staff.

Jen Hamiltno (09:43.738)
This is such an important question. It has become critical since the great resignation. But I think that we’re not gonna have just this phase of the great resignation. I think things have been changed forever. So the work, I think the win in the work is through your workforce. If you can nail the recruitment and the retention, you can get ahead of your competitors. Some of the great, some of like the…

logistical pieces is to really be clear that you now are your biggest asset is your people. And I don’t know whether you’re in professional services or not, but way to get them to want to be a part of you. First and foremost, they care about culture. I don’t care. I’m not talking about a certain age, but everyone is now realizing I want to be a place that is fits for me because COVID helped us realize like, I don’t have to put up with this stuff.

So they want to be around other like -minded people. So that can also go from just like they’re high performers. You want high performers, you need high performers on the team. They want to be with like -minded people. They also want to be with like -hearted people. So having a mission that aligns you. So all of those culture pieces, when the day is done, that’s what’s going to attract them, knowing that they can have that. What’s going to keep them is knowing that it’s not just some false promise. The other little logistic,

tip, if you will, I love to tell people don’t just have HR people put together a position description and put that out for posting. Have a collaboration between your marketing folks and your compliance folks and your HR folks to be able to create something that you post the position that is actually more marketing based. In other words,

It’s not about just filling your seat. It’s about what’s in it for that employee and finding that marriage. And so being able to communicate, this is what we need from you, but this is what you get from us.

Anthony Codispoti (11:48.136)
That’s really good.

What, other than some of the things we’ve are… And give them good benefits. Yeah, I like that.

Jen Hamiltno (11:52.57)
and give them good benefits, right? It really does make a difference, right? Because you’re honoring your people. So all joking aside, it is important to show that you care and expressions of that your family matters, your health matters, not just the actual benefits, but being able to.

say that you matter and not offering the benefits like it’s inconsistent in your messaging. So it is a whole package.

Anthony Codispoti (12:23.399)
Now, aside from some of the interesting things we’ve already covered, Jen, what do you feel sets you apart from maybe some other fractionals in the space?

Jen Hamiltno (12:33.274)
One of the things that sets me apart is that I bring in other fractionals. So my approach is bringing in the right person for that team. So I partner with many, many solopreneurs or small firms. And if I’m not the right one, I’m really more of a matchmaker. Sometimes I’m the right one, sometimes I’m not. And I see that where the clients are best served and where I’m gonna get the best…

bang for my buck, which is in making a bigger impact, that’s really what I’m about, is having the right person in the right seat. So that is not always me and I’m okay with that, but I’d rather have the connection or the introduction. So that’s one piece of it. The other piece is that I’m very much focused on the strategy and strategically knowing what does it take to actually have a strong, healthy,

business and not just like putting out fires. So a lot of times it’s very attempting that when you come into a company that doesn’t have someone like our kind of brains, the analytical, the execution mind that you focus on that, help me solve this problem, help me make this decision. And so that is needed, but you need to also be pushing for, we need to strategically grow your infrastructure and head towards your goals.

and figure out how to get there. So I’ve created the six pillars of business that are based on valuation, meaning a company can go and say, what’s the value of my company to experts, different accountants than me, but other accountants who can say, here’s the dollar value. But what they’re really saying is how healthy or how risky is your company? So something uniquely I do with my clients is I look at what do they look at?

to grade a company’s health. And then I set up the strategy and the structure to basically build something that a valuation expert would give it a healthy grade, if that makes sense.

Anthony Codispoti (14:40.165)
Yeah, interesting. Let’s shift gears and talk a little bit about the Fractional COO Collective. What was the inspiration behind starting this and what is it all about?

Jen Hamiltno (14:50.138)
So the Fractional COO Collective is a place where fractional COOs are, for those who run on EOS, they call them integrators, but same sort of role, where we come together, we come together in a round table environment every month, no charge to that. And part of it is that there’s something special about being with peers. We talk about what uniquely is in our role, challenges and opportunities. So the things that are challenges, opportunities for us.

are getting the clients and then serving the clients. And so our topics are around that. But it’s so beneficial to hear from peers how they’re doing it and ask questions and hear their ideas. So the reason I started it is because I wanted that. It’s very selfish. I wanted to engage in those conversations. I wanted to learn from others. And I’ve already mentioned I love mentoring. And so I would often be asked,

many, many meetings, no compensation, one -on -one with other fractional COOs. Like, how do you do it? What do you do here? And so part of it was selfish, is that I wanted to have a place where I can continue to learn from others, but they could learn from me and from others like me. And I didn’t have to fill my calendar with a lot of mentoring meetings that I could do it together. So I first looked for where…

would this community be so that I can join and contribute and be a part of it? And I didn’t find one. There are COO communities, there are integrator communities, but they’re full -time and fractional. There are fractional leadership communities, which are great. I mean, I’m a part of all of these as well, but there wasn’t one just for fractional COOs. You know, it was like fractional CMOs and fractional.

CTOs and all of these things those are great too and I and I think each area of community is helpful to have But because I couldn’t find one I said I’m gonna stop looking and start leading

Anthony Codispoti (16:50.469)
And so how did you sort of kick this off? How did you get sort of the first base of people to…

Jen Hamiltno (16:57.306)
So I do have a decent network because I’ve had so many, I’m part of these different communities, so I’m known as someone with FractalCO, so a lot of folks that are connected to me in my own kind of Rolodex, as well as the famous LinkedIn Rolodex. And I just started by doing a monthly roundtable. So I picked a topic that was of interest to me, put it out there. The first time I think I had about 20 people sign up for it.

And about, I want to say maybe 10 showed up and they’re like, gosh, Jen, this is really great. And it was really great for me too. So then I said, you know what, I’m going to do this every month. I pick a different topic every month. It’s relevant for us. And I’ve had my last fractal COO for June was last week. We had over 80 people sign up and about 26 people came at about five other people were like, dang it. I missed it. I wanted to be there so badly. So.

and what’s a good sign to me is that people are coming back and wanting to show up and are upset when they miss it. And again, it’s, it’s about the conversations, not just about me. I’m sure, you know, any, you can put any COO in there. We’re by our nature, good at, at, facilitating a good discussion, but to have, this safe space, we honor confidentiality and the safe space to share is pretty magical.

Anthony Codispoti (18:24.74)
And so what is the actual structure of the get together like? Are you sort of leading the topic? Does everybody sort of get, you know, three minutes to kind of ask a question or how do you lay it out?

Jen Hamiltno (18:34.714)
Great question. I like to lean into the like I had mentioned before, why are we here? And that culture, you know, it’s important whether you’re in a company or whether you’re in a community. So we really get grounded in the heart connection, the mind connection. So we start with why we’re here and the impact we can make in small businesses and how they need our brains. And then we do some heroic wins. So do a few introductions. I love to

to share what are some things that people were able to accomplish so we get some understanding of the things that we can create. And then about 40, 45 minutes the rest of the time is I have one topic and I usually create three different questions related to that topic. So I’ll put out the question and sometimes I answer first, sometimes other people answer first, sometimes I answer first totally because they need someone to get it started.

But man, after that first one, we have folks that are contributing to answering that specific question. And then sometimes they’ll ask more questions of each other. But lately it’s gotten so big, I actually put them into breakout groups now where they answer the questions. We come back from the breakout group and then we get a collection of what are some of the favorite things they heard in their groups so we could still hear from the larger group. Then ask the next question related to that topic, go in the group and again, come back, reflect.

And so we kind of, I strategically put the questions in order to kind of deep dive and to build on them that we can get towards action. The end of the meeting, one of my favorite things as ACOO is to make sure people do something. Don’t just talk, do. So we ask people to make a commitment and have them either share verbally or put it in the chat, but write down what action out of what they heard, what something they’re going to do with this information. And I think that.

helps have that group accountability by putting it out loud. But also, I don’t want people to come where they’re not getting value. So having them stop and reflect, what can I do with this information, makes it more valuable, not just for them, but for their clients and those that they are able to do something with, what they learn from this amazing, kind of mastermind -like experience.

Anthony Codispoti (20:52.676)
You mentioned one of the things that you were hoping to get out of the collective that other fractionals are looking to get to is how to find clients. I’m curious, what does business development, what does the sales process look like for you?

Jen Hamiltno (21:04.154)
So for me, it’s really about listening first and truly understanding and evaluating, asking enough questions to understand what are the foundational pieces that are in place, because I don’t want to work on what’s already working. We don’t want to break what’s working. And then secondly, I look at what are the foundational pieces not in place. From going through those questions, understanding where they’ve been, where they want to go.

then I’m able to put together a customized proposal with a few different options to be able to let that client know, here are different ways. If I, back it up a step, if I’m not the right person, I will bring in another person and I’ll tell them, because I can tell usually from those first questions if I’m going to be the right fit. And I will tell them before I put a proposal together, if I’m going to bring in somebody else or if I fully refer them to,

Sometimes it’s not even a COO. Sometimes what they need is a project manager and they would be overpaying. So, you know, I have a lot of good resources or sometimes they need an executive assistant. So part of it is just kind of pointing them the right direction. If it is something where I’m a fit or one of my colleagues is a fit, then I put together that proposal that gives them different options. But I like to say that it’s a draft and that the client and I are finalizing it together because it’s meant to be a partnership.

when we start working together, so why not have it be a partnership before we start working together.

Anthony Codispoti (22:37.124)
Nice. What are some of the most common mistakes that you see clients make?

Jen Hamiltno (22:42.586)
The biggest one I think that I’m trying to think like universally, it’s failing to delegate appropriately. Because man, it hits everything. And I get trapped in it too. We get trapped in the idea that no one could do it as good as me. It’s gonna take longer to train them. By the time I teach them, I’ll do it myself. You know, like all of these conversations we have to justify just doing it.

Anthony Codispoti (22:55.684)
your team.

Jen Hamiltno (23:11.994)
And so it’s overcoming that. It’s also there’s a fear. This is your baby. This is what you’ve created. You’re putting so much on the line that you want it to go well. And so the fear of being out of control and not being able to control it is at the heart of a lot of these things. So that’s where the mistakes come in. And then sometimes…

It’s like, my gosh, I know I have to delegate and they just throw it at someone but not set them up for success. And that goes poorly. Often this happens with like an assistant. I’m going to like, finally I’ll get an administrative assistant. Right. And then they’ll never do it again because they’re like, that didn’t work. See, I was right. All my fears came alive. And yet what they’re missing is like how to delegate appropriately. So yeah, that’s one that you can like.

be whether you’re bringing on a consultant, whether you’re bringing on a new team member, an outsourced resource, that handoff, whether it’s you to someone else or your team to someone else and getting that delegation culture appropriate delegation, it really can stop your growth and it can really add to your stress. But if you turn it around and you do it right, that’s why for me, people is so important. They can.

Absolutely change your world because there is a way to be in control. There is a way to trust It’s just how you pass that on to someone else to take it and run with it makes all the difference

Anthony Codispoti (24:45.028)
Slightly different question, but similar. What’s some low -hanging fruit for most companies that if they just did these one or two somewhat simple things, would make a big difference in their business?

Jen Hamiltno (24:57.338)
So I’ll go with a similar piece. One is I almost always am looking at, especially for the business owner, what are the administrative things that you are doing? I was talking to one yesterday and she’s got this company she’s had for over 20 years, really successful, good sized team. She’s still doing payroll. And I’m like, my goodness. You know, so what are the things that administratively that you should no longer be doing at the stage that you’re at and or start?

to delegate off to people who can do it probably better than you to free you up to do the things that are best for you. The other low hanging firm, so that’s an easy one because you could start with a part -time administrative support. You can grow into it, you could try different firms. I love to be able to just start to pull things off of their plate. The other one that’s relatively easy,

is I would challenge most people to look at what are they charging. It may not mentally or emotionally be easy, but it is relatively easy to grow your revenue and hit your profitability because your prices are too low. And I say that because we as humans, and I will throw myself under the bus on this one, I work with a lot of female entrepreneurs, not only female entrepreneurs, but a lot of them were really good at undervaluing ourselves.

So being able to just get your prices to the place where you have some freedom to invest in your company, have profitability to reinvest in your company, cover the costs you really need to pay, including yourself. A lot of times we don’t pay ourselves market value. So increasing your fee and really getting yourself out of your comfort zone. How can I?

charge more does have a ripple effect that allows you to do some of these other infrastructure things.

Anthony Codispoti (26:58.052)
Aside from boosting up your prices, what’s something interesting that you’ve done to encourage clients to, I don’t know, maybe lower costs or increase sales, other ways, other interesting ways to increase profitability?

Jen Hamiltno (27:13.498)
I’ll do one on each side. So on the sales side, I know it sounds rudimentary, but really putting asking for referrals. So in upsells, so a lot of times you just kind of put your clients or your customers on autopilot and forget that they are likely satisfied, if not fix that, but likely satisfied and can be a resource for you.

to continue to make an impact, to continue to serve or support. And so people will say, yeah, I asked for referrals, but do you have a system? So you’re systematically asking for referrals and systematically finding what’s the next thing they may need. Honoring that person, not doing it just out of because I need to, but a system around it. That’s what most people are missing.

So by putting these things in place, you don’t have to think about it, you don’t have to remember, and we’re doing it at the right time, it’s right time for the relationship. So that’s one on the sales side. On the expense side, it’s really about, again, you can hear I’m all about people and delegation, it’s really about getting work off of the plates of people who shouldn’t be doing that job. So a lot of people will say write people, write seats.

But a lot of times it’s not just the business owner, it can be leaders, it can be, you know, I threw it at this person because they’re so nice and they get it. But if you, the work we really do, and this is fundamentally what we do is create a corporate structure, what are the roles you need, then put the right people in those seats, seeing your holes and putting people that love that job, that are skilled at that job, that are natural at that job in there.

What happens is you have incredible efficiency because people who are good at it and natural at it are going to do it better. But you’ve also relieved work that flows your high thinkers down or your really good leaders down, whatever. And so you now get efficiency because you’re getting the most out of your, if you will, your investment in their skills and their talents. And so it’s like getting everyone in to be there in their talent space.

Jen Hamiltno (29:26.522)
naturally creates efficiency. So you’re getting basically a better return on your labor investment, making the fact that your expenses can go down because you’re not having as much waste, but you’re also being able to get the most out of your people, really increasing your productivity.

Anthony Codispoti (29:47.422)
You mentioned having a system for referrals. Do you have some suggestions? Good structures you’ve seen?

Jen Hamiltno (29:54.202)
So part of what I do is continue to learn from other mentors myself, which is part of why I love mentoring, because it works for me. One of my mentors is Darren Hardy, and I love what he teaches about the referral system, is if you map out the customer journey, there’s highs and lows, just naturally part of what you do. And you’ll be like, no, they’re always happy with me. If you look, there may be times where you have to give bad news, or you have to give them, maybe there’s a return if it’s a product.

You have to tell them like the things they don’t want to hear if it’s a service, right? So you don’t want to ask then in the lows. And then there are just natural times where like, gosh, you got to win or there’s, you know, you accomplish something together in your relationship or they’re really happy with the results that they got out of your product or service. Those are the strategic times you want to ask for those referrals. And the other side of it too, that is not to say, can you give me a referral?

But can you introduce me to someone that has this problem and would like these results, right? Because referral, the word referral is very weighted in my reputation is on the line. And if you other person, even though you’ve done great for me, there’s that hesitation of like, but if you screw up my friend or my family member or my colleague, I’m going to look bad. So you want to take away their risk of their reputation riding on you and just

ask for an introduction to other folks and then also have something that they can get from that. So I often say for referrals that you can get a free office hour with a COO. Your people, if they want to pick my brain and be able to just come in with one issue that they have no one to talk about with and want to just figure out how to make a decision or what’s one thing they can do. I say that’s what happens in my

free office hour with a COO and then that gives them something to give them and say you’re going to get something for it. So it’s when, it’s what you say and then what they get to give to that person so they look like the hero that they’re helping them out.

Anthony Codispoti (32:10.524)
I really like that because it highlights the importance of word choice, right? Like you said, referral sounds like, my reputation is on the line. I don’t know if I want to do that. But if it’s like, hey, do you know somebody who has these problems that could benefit from this solution? Would you please make an intro? And as a thank you, if you do, here’s, you know, in your case, a pre -hour with a fractional COO to get some consulting. Maybe it’s a gift card or it’s, you know.

whatever you can offer. I think it’s pretty creative.

Jen Hamiltno (32:42.074)
Yeah, exactly. Thank you, Anthony.

Anthony Codispoti (32:45.468)
What’s a serious challenge, Jen, that you’ve had to overcome in your business or personal life, and what did you learn coming through that experience?

Jen Hamiltno (32:55.482)
for me and I bet you others in, especially if COOs, because of our mindset and in other service providers probably are the same thing. It’s the guts to go and do it on your own. I kept chickening out and so I would join other firms and hope that, you know, my idea of how we could do this thing I do better, I could influence or be able to do that in somebody else’s house, essentially. And,

No one really wants someone else to reorganize and clean their house. They kind of want it the way they want it. So I would move to different firms being afraid of what I inevitably knew I needed to do, which was go out and go out on my own. I now am on my own. So I’m excited to say I’ve learned that less than the hard way many, many times. And while I’ve loved the people I’ve worked with,

I realized that I’m not honoring me and I’m not honoring them if I’m pushing for a different vision, a different way than what it is that they want to do. And so to me, that was my sign. I needed to go out on my own, but I was scared. And I mean, six years of scared and probably I want to say like five different leaders hoping I could make it work where our visions were close enough that I could like, Ooh, this is where I can make my magic happen.

And yes, we had great successes and things, but there was always still something inside of me gnawing at me saying, but you’re compromising in some way. And so finally, with the support of accountability folks, my own coaches, I was able to, to realize that I’m never going to be satisfied in some cleaning someone else’s house.

I am ready to do my own entrepreneurial journey and my vision is important to me and I think I can make a big difference and inspire others to do the same. And if I keep hiding behind another leader, I’m not going to be able to do that.

Anthony Codispoti (35:00.059)
What are some of the things you felt like you were compromising on at the other firms? What was it about yourself that you weren’t allowing to come through?

Jen Hamiltno (35:08.25)
I, that vision in that I saw a different need in the market, a different need in the world, if you will, than what the folks that owned the firms that I was a part of. And while there’s nothing wrong with what they had, I was compromising, like telling myself it’s close enough to what they’re doing. And yet I just saw something different or bigger in different cases. And so that’s.

That’s not one you want to compromise on. The other thing I would say is values. And I don’t mean there wasn’t a core value alignment, although sometimes there was. But the things that I value, and so in terms of my approach, I really lead with that the client is important and then get a team that loves to provide client excellence.

Whereas there’s other cultures where you can get a great team and then they’ll make magic happen for the client. As subtle as that sounds, that is a huge difference. Everything in your marketing, in your approach is very different when you look at, am I about customer excellence or am I about team excellence? Now I’m about both, but you can’t have both at the same time. You have to pick one. So for me, I was in areas where sometimes their team was…

It was about the team or their own family or their own vision more than the client. And so that was an uncomfortable compromise for me that I had to stop. That I have to do what’s best for the client. That’s where my heart is. That’s where I shine. That’s where I really, yell my best that I can give my best. And then I’m now in my own firm surrounding people who are the same. Like there’s such a joy out of seeing the results for a client, not just for yourself. And so.

Again, nothing’s different. It’s different, not bad. You know, it’s just different approaches. And so to be able to be very, very clear, what is my vision? What are my values? What is my focus? Allowed me to say, stop trying to force other people in their own company to do it my way. It’s time to do my own.

Anthony Codispoti (37:22.138)
I want to hear more about what led you to that courageous moment to make the decision to go off on your own. Six years of going, you know, a couple of different firms, having success there and doing well, but always knowing that there was something else inside you that you wanted to have come out, that you wanted to make happen. And for six years, holding yourself back, holding yourself back, and then something finally clicked. What was it?

Jen Hamiltno (37:53.658)
I think it was more something finally kicked, not clicked. And it was myself kicking my own butt and the people that I trust, I’ve had for many, many years to say my accountability partners and their belief in me and their reminder of me echoing my complaints and that I’m in a pattern really helped me see that.

The solution isn’t go join another firm, because I had tried that many times. But my own butt kicking was looking at my results. Not just my own financial income, although sometimes that’s like, gosh, you know what? I feel like I can do more. It’s not the only motivation. But looking at the results of what I knew, the impact I could make on, for me, I’m passionate about small businesses succeeding. And,

I wasn’t able to do it as much. And so for me to have to put my head down at night and to stare at the ceiling, the things that we do, we really look at night, what do we do wrong, essentially? We wake up in the morning excited what we could do, right? But the nighttime reflection is like, man, I wish I would have said this differently or done this differently. I had too many nights where I was kicking my own butt saying, you know what?

It’s not enough. It’s not right. You’re, you know, you’re out of integrity. You know, you can do something different. And so I like to go back and sleep at night and be like, man, you, you really honored what you’re committed to, where you’re going, the people you work with, the clients you have. And not that I didn’t, but, but there were always little pieces that I’d like, but it could be more. And so I was tired of kicking my butt in that way. Cause it’s.

It’s not as fulfilling as I knew this could be.

Anthony Codispoti (39:50.585)
So what I like about what you said is obviously there was a lot of you kicking your own butt. But you also mentioned a really good support system that you have. People who were there being a positive voice, being an affirming presence for you, reminding you, you’ve got what it takes, you can do this. And I’d like to hear more about that crew because I think a lot of times people look at business leaders and they kind of put them on an island. It’s like…

This person is amazing, they’re strong, they’re independent, they’re pillar, they stand well on their own. And man, it’s so much easier when you allow the people that you trust that are close in your lives to be there and support you and help you when you need it.

Jen Hamiltno (40:36.442)
I can’t recommend more that you surround yourself in some of something ongoing recurring accountability type group whatever you want to call it mastermind that kind of thing. So I do this and then I have my own coach and so I do this in two ways every Monday I meet with the same three women and a half since November 2019 every Monday sometimes we’ll take the holiday off but what.

It’s not just any people, it’s people who aren’t afraid to tell you directly, tell you straight kindness, of course, but there’s very few people on the planet, if you really look in your life, who will tell you the full truth and get in your face because they’re standing for your greatness and they know what your potential is. That’s what I have in my coach. That’s what I have in these women. And then I meet with my coach every Tuesday.

And so that has been, gosh, I want to say maybe eight years or something, a long time. So I know him really well because we do a trade. I coach him, he coaches me. So it’s a really nice, and I see so much, that’s also why I’m a big fan of mentoring, is that I see so much in him mentoring me, but I also see so much in what I say to him. Am I following my own advice?

So I think it’s a mutual. It’s not just them standing for you. It’s who’s standing for you, how they’re going to stand for you, and how you stand for them. Because I always say where my breakdowns come from, I’m not taking my own advice. If it was a friend or if it was a client, what would I tell them to do? That’s what I should be doing.

Anthony Codispoti (42:18.519)
For people out there who are listening and say, wow, that sounds pretty powerful, I would love to have something like that in place for me. What advice do you have for them to get started? Do I need a group of four people? Is it enough to be one on one? What are the sort of criteria or the check boxes that I should be looking for?

Jen Hamiltno (42:40.058)
My answer to that, should it be one -on -one or four people, I say yes, whatever you can get started with. My one -on -one, well, let me back up. Where I found both of these people were different communities. One of the things you hear, I’m super committed to communities, finding like -minded people. You get to filter out. Well, first of all, if you’re coming to this thing for a similar reason, you know you’ve got some alignment already. So you wanna find where you align. So maybe it’s the way you’re being taught.

Maybe it’s that you have a similar profession, whatever it is. But that’s a great place to go find people is that you’re already kind of committed into the same kind of group. So that’s where I found them, two different groups. And then I would be very selective and very straight with what kinds of expectations you all have of each other so that you can be confidential, so that you can be straight with each other, that you can be direct.

that you can know it’s safe. They’re not going to use this information against you, those kinds of things. But then also the commitment of time to each other. So one of the things that we tested out with this group that is the four of us on Mondays, we started with eight, then we had seven, then we had five, and we ended up with four. And so you’ll know who shows up. And if at some point they stop showing up, go find a new one, start a new one.

Anthony Codispoti (44:09.271)
That’s great. Jen, what is something you wish you could teach a younger version of yourself?

Jen Hamiltno (44:16.406)
There’s a long list.

Anthony Codispoti (44:21.463)
Pick one or two, the big ones.

Jen Hamiltno (44:22.586)
But I’ll pick one, but I think that we could probably all say that there’s a long list. The biggest thing I would say to myself is that it’s okay that you’re going to have a not traditional path through your career. I think that I’ve made myself very, very wrong from following my heart and my skills and my vision.

And instead now looking back and being in such a place of joy, fulfillment, where I really get to make the biggest difference. I had to do accounting and then go into a nonprofit and do, you know, like I have a peppered background of experience, right? It’s not a straight line and it’s okay. And it’s, I needed that, you know, so I think there’s a lot of like, man, am I failing this? Cause I didn’t like it. I’m trying something else.

Instead of making it wrong, I would say make it right, that just follow the path. It’s the path that’s there on purpose.

Anthony Codispoti (45:27.415)
What’s a fun fact that most people wouldn’t know about you, Jen?

Jen Hamiltno (45:32.026)
My favorite fun fact to share is, so first of all, I don’t know how much you can tell because this is Zoom, but I’m not a very large person. I’m 5 ‘4 and I’ll just say somewhere around 125 pounds. And my fun fact is that twice a week I do jujitsu, mostly with men who are about 200, 180 to 200 pounds. And I haven’t died yet.

Anthony Codispoti (45:59.541)
What’s the attraction to jujitsu? What do you like about it?

Jen Hamiltno (46:01.658)
So I’ve been doing this for about six and a half years and I think it’s been about six years and five months that I asked myself that same question. I don’t know why I keep doing it and yet I do. Part of me is like there is no logical reason you should do this. What I do like to do is that the world of entrepreneurs and being a leader, having difficult conversations is hard.

It’s very hard, but it’s like emotionally and mentally draining. So when you do something so physically challenging where you literally can be choked, you literally can have parts of your body broken off and you’re choosing to do that, it allows me to believe in myself at a deeper level of confidence and it helps give me perspective that I can do hard things.

Anthony Codispoti (46:54.549)
For people who don’t know, maybe describe a little bit Brazilian Jiu Jitsu. It’s grappling, it’s kind of wrestling, it’s like it’s very physical.

Jen Hamiltno (46:59.194)
The best way to explain it is wrestling. So if you put a little woman with a large man and say, go ahead and wrestle, you probably would not put the odds on someone my size.

Anthony Codispoti (47:11.414)
you hold your own? Do you do any competitions? Or is this just for…

Jen Hamiltno (47:15.45)
yet mostly because I stink. I’m not that I’m not naturally you know like I had said before it’s really you can find your strength when you’re in your natural environment. This is not my natural environment and so I don’t trust myself with people that aren’t in my academy where I learn to take care of me. Meaning I don’t

I love that these gentlemen will listen to me if I say, you know, you’re squishing me and I can’t breathe or tapping, you know, that kind of thing. And so they really have a culture of respecting your partner. So I feel safe there and I’m a little afraid to, like, I don’t really want to be broken. I do want to show up to work. So as much as that it’s possible by accident, I’d say in my academy, it’s not always.

I don’t want to say intentional, but it’s not as easy when you’re not used to working with people for them to know your signs or see that like, hey, this is too much. So that keeps me, there’s still a little bit of fear in there, if that makes sense. But I like to think it’s smart fear.

Anthony Codispoti (48:29.013)
Yeah, I mean, safety first, right? I love what you’re saying. I mean, it’s a very physical endeavor. You can’t help but turn off sort of the thinking part of your brain. You’re just in sort of like, you know, fight or flight, like reaction mode. And that’s good. Like, you know, as people who are doing very cerebral jobs all day, we’re stuck in our heads. There’s a lot of chatter that going on up there. To be able to find something, an outlet where you can turn that off.

is refreshing, rejuvenating, right?

Jen Hamiltno (48:59.354)
It is. I do get more present. You’re talking about being in the moment. You have to be. If you don’t pay attention, that’s when you can get hurt.

Anthony Codispoti (49:09.364)
Jenner, are there specific mentors or books that have been helpful to you or your professional career?

Jen Hamiltno (49:17.434)
Yeah, so me as a leader, I started with a lot of the great books of like Thinking Girl Rich and how to win friends and all of that kind of stuff. And so there’s a lot of the classics are classics for a reason. So I recommend those. As I mentioned, one of my favorite mentors, I love his courses. I love what he stands for and I bring it into my work oftentimes, but I also continue to grow is through Darren Hardy.

has great free stuff and great paid for stuff and I invest in it all because it really does make me better. One of the things that I say for as a COO, some of the better books for my position if you’re in that position, Traction is a classic, E -Myth is a classic, Predictable Success is a newer one that I really appreciate and have brought in.

Not as well known, I think Wes McClellan is the name of the author. That’s a really good one. And then if you get into also the most business owners and even some COOs are not as comfortable with the numbers. So, Grave Crab Tree has a book called Simple Numbers. That’s a great one too. So, it kind of gives you, I like to look at the strategy, the business approach, the structure you need, and then also just like the numbers you need.

as well as leadership, that’s like what my job is all about is those bigger pieces. And so hopefully that’s a good kind of a bouquet of things that will help COOs out there.

Anthony Codispoti (50:54.195)
That’s terrific. Jen, I just have one more question for you, but before I ask it, I want to do two things. First of all, if you’re listening today and you like today’s content, please hit the subscribe, like or share button on your favorite podcast app. The second thing I want to do is tell people how to get in touch with you. They listen to your story today. This is interesting. I want to learn more. I want to learn more about the Fractional COO Collective. How do they get in touch with you?

Jen Hamiltno (51:17.306)
The best way is through email. I’m also on LinkedIn at Jen Hamilton, but you might find there’s a few of us out there. So start with email and then we can also connect on LinkedIn. So Jen, J -E -N at Hamilton COOs with a plural S dot com is the best way to reach me. And I, again, like I had said here, if you’ve got something you’re dealing with, you want to take advantage.

on behalf of the company and being able to share this, one of those office hours where you can think through some of those challenges. I’m more than happy to do a complimentary answer. You can email me and let me know. Yeah. Thank you. It’s fun. I mean, I can’t deny it that I enjoy being able to hear business problem and then work together with that leader to solve it.

Anthony Codispoti (51:53.235)
Wow, very generous. That’s a very nice offer.

Anthony Codispoti (52:06.899)
It’s kind of how your brain’s wired, I can tell. Like you enjoy, I’m curious, do you like jigsaw puzzles? Because you’re kind of figuring out business puzzles in your head.

Jen Hamiltno (52:13.658)
Yes. Yeah. Yes. I do love solving puzzles. I should like chess, but I haven’t learned it yet. So, but yes, that kind of those types of games are fun for me.

Anthony Codispoti (52:28.786)
Yeah, so last question for you, Jen. I’m curious, how do you see your industry evolving in the next five years? What do you think the big changes are that are coming?

Jen Hamiltno (52:37.754)
So for the fractal COO, if I get specific in that industry, what I do see is more and more people trying it out because it’s becoming known and more and more people failing if they don’t invest in themselves to know how to nail the marketing and sales side of it type of thing. And so I really hope that’s not the case. It’s part of why I do what I do because…

we are so needed. So that’s the other side of what I see as the trend is that as the solution for these small businesses becomes more known that a fractional COO can actually help me with these things that have me stressed out or stuck or hitting a plateau, their demand I think is going to go up. And so it’s a matter of for me really having the ability, like I feel my role in that and that

creating that future that has the balance work is advocating and educating small businesses. So I appreciate Anthony the opportunity to share like what’s possible without having it be a major budget hit by having that this kind of brain in your business. And then also what’s possible for fractional COOs to know that you can do it. You can join a firm like I did, but if you really do have that nagging feeling inside and you want to do it on your own, don’t be alone.

And that’s why I say it, be a part of our community, get some help, do something to make sure you get over the scary part of having to do business development.

Anthony Codispoti (54:12.625)
is a great resource for fractional COOs or aspiring COOs. Well, Jen, I want to be the first one to thank you so much for sharing both your time and your.

Jen Hamiltno (54:23.834)
Thank you for having me. It’s my honor. Thank you for what you do for the world because folks like you that are serving clients make my job a little bit easier. As I said, it’s all about the people. I don’t care if you’re in professional services or not. And if you can have those people want to be a part of the team, feel honored as part of the team, feel seen as like what they need for themselves and their family is important, it makes my job easier. So thank you.

Anthony Codispoti (54:49.713)
That’s wonderful. I appreciate you saying that. Folks, that’s a wrap on another episode of the Inspired Stories podcast. I appreciate you learning with us.