Participants
Hosted by Isaac Sacolick, CEO of StarCIO
Special Guests
Digital Trailblazers
Summary
The episode focused on discussing entrepreneurship and the challenges of becoming a solopreneur, freelancer, or startup founder. Isaac hosted a panel of experienced entrepreneurs, including Tyler, Heather, Derek, Liz, Joanne, Martin, John, and Joe, who shared their personal stories and insights about taking the leap into entrepreneurship. The panelists discussed topics such as resilience, risk management, experimentation, and the importance of having a clear business model and market fit. They emphasized the need for networking, honest advisors, and a well-thought-out go-to-market strategy. The conversation also touched on the financial and personal challenges of entrepreneurship, including healthcare costs and work-life balance. The panelists agreed that while entrepreneurship can be rewarding, it requires careful planning, a strong support system, and a willingness to adapt and learn from failures.
StarCIO Research
Sources
- 80% of small business owners say they would still start their business if they had to do it over again. U.S. Bank
- Total full-time self-employment in the U.S. hit its highest annual level on record in 2025, with about 16.77 million people self-employed full-time – SBE Council
- Total Entrepreneurial Activity in the U.S. is at a historic high: 19% of adults are actively starting or running a new business – GEM
- Globally, roughly 20% of adults are involved in entrepreneurial activity, around 582–665 million people. TKG
- •40% see good opportunities but won’t start a business because of fear of failure ERC
- •A 2024 founder mental‑health study reports 93% of founders show signs of mental health strain, with 55% experiencing symptoms weekly or daily. Foundology
- •67% of founders work more than 50 hours per week Sifted
Transcript
[00:00:00] Speaker A: Hello, everyone.
[00:00:03] Speaker B: Hello.
[00:00:03] Speaker A: Hello. Hello everyone. Welcome to this week’s Coffee with Digital Trailblazers. I’m psyched to be here. I didn’t hit the Go live button yet. Here we go.
Hello everyone. Welcome to this week’s coffee with Digital Trailblazers. Our 161 first episode. I am so psyched to be here. Thank you for joining us. This week we have a very exciting episode celebrating Natural Entrepreneurship Week, which is a US event. I don’t know a whole lot about it, but I’m excited to be a part of it and use it as a way of celebrating one of the many opportunities facing Digital Trailblazers leaders who are looking to try something different, maybe become a solopreneur, maybe become a freelancer, maybe join a startup or a growing company, or even look to become a founder and start your own company. So we’re going to look at all four of those options for everybody here who are either part of that experience or thinking about joining that experience of going on your own.
And I asked my panelists, every one of my panelists here today, every one of our speakers is either doing this today or has done it at least once in their career. I’ve asked all of them to share their personal stories. We talk a lot about storytelling here.
So folks, think about how you want to represent yourself and how you made your decision to go solo or join a startup or even found a startup. But before we get started, let me share some stats with you. I think this is really important to get a sense of where we are in the world globally and where we are in the US Around Entrepreneurship this Week National Entrepreneurship Week is a Congressionally chartered week dedicated to empowering entrepreneurship across the United States.
The graphic on the right is one of their banners. You can see the URL there. To find out more information about it, some Data I found 80% of small business owners said they would start their business again if they had to do it over again, which sounds like a pretty good statistic. But that also means 20% said they might not do it again.
Some metrics on the size of our audience, the number of people going into startups and going solopreneur, becoming a freelancer.
Self employment in the US Is growing at the highest annual level on record in 2025 at 16.77 million.
That’s from the Small Business Council. Total entrepreneurial activity is also at a record high. 19% of adults are actively starting or running a new business. And then globally, roughly 20% of adults are involved in some kind of entrepreneurial Activity. It’s quite impressive. We’re all trying to become our own digital trailblazers. However, there are some considerations. Right.
I’m going to share a movie scene that has always been part of my psyche. And I don’t know how many of you have seen Rounders.
If you haven’t, it’s a great movie. It is a poker movie. It’s with Mount Damon. It’s just a lot of fun. In the opening scene, he’s driving a truck and doing deliveries and he talks about the where he was in his life. He was a poker player, hadn’t made it big, lost out. And he comes back and says, you know, you don’t read about the people who tried and failed. And so there are some considerations when you think about going off on your own. 40% see good opportunities, but won’t start a business because of fear of failure.
I can tell you from experience, I had one of those startup ideas that I passed on because of that. A 2024 found mental health study found that 93% of founders show signs of mental strain, with 55% experiencing symptoms weekly or daily. It is a hard life and many founders, 67% say they work over 50 hours a week. So lots of reward, lots of flexible scheduling, lots of going after your personal passions and certainly a lot of opportunity to strike Richards in going off on your own. But also a lot of realistic considerations. Everybody here has to think about if you’re going to go off on your own, particularly if you’re going to become a solopreneur.
So that’s our topic today. I want to welcome our, our guest Derek. Heather’s here, Joanne’s here, John’s here. Joe and Liz are here. I want to welcome back.
Who am I missing here? I think I’m missing someone. Martin, I think is here. Yes, there’s Martin. I want to welcome back Tyler Johnson who is a semi regular speaker here at the Coffee Hour. And Tyler, let’s start with you. I want to get your stories, I want to get everybody’s stories. What was the turning point that pushed you to take the leap to entrepreneurship and to become a founder? Tyler, I think you’re in startup number two.
So glutton for punishment maybe. I know you have a background working in enterprise software and technology sales. Give us a little bit of background. What made you do the pivot?
[00:05:53] Speaker C: Well, thank you for having me, Isaac. I really appreciate the insights that the panel that you put together every Friday brings. So speaking of storytelling, let me tell you a story. So early in my career at Hewlett Packard. I worked on a $8 billion Superdome supercomputer product line.
The team was full of PhDs from places like Stanford. I was just a bachelor double E from FAU and Boca Raton. I wasn’t the smartest person in the room, but what I did have was cross domain exposure. Before hp, I worked at TRW and Automotive. I learned lean manufacturing. I saw how physical production systems eliminate waste, reduce bottlenecks, and you design for flow. When I got to hp, I realized we were treating software testing like artisanal craftsmanship instead of a production system. So what I did was I applied lean principles to engineering validation across domain application.
The term DevOps, by the way, hadn’t been invented yet, but that’s exactly, exactly what we did. We automated simulation testing more than double productivity of the engineers and proved quality dramatically.
And as a result, I ended up with 22 patents from HP. That was entrepreneurship powered by pattern transfer across industries.
So for me, the turning point came later. I kept seeing the same pattern, same issue across companies where you have compounding complexity, integration costs growing exponentially.
And you know what often gets labeled as innovation is really modernization or innovation theater. An ERP upgrade and new HR system. This is motion, but it doesn’t represent change.
Leadership turnover is accelerated, incentives are shorter term. It’s harder sustain multi year innovation inside large corporations than it was 20 years ago.
So for me, walking away meant straight trading, stability, title income for uncertainty and stress.
If you’re somebody, you know, like me, that sees these cross pattern, cross domain patterns, you also see that the system can’t evolve from within the constraints of the corporation. And you know, for me it was hard to unsee that.
So eventually I found that I needed to move out to entrepreneurship.
[00:08:41] Speaker A: Awesome. Tyler, I wrote this statement here just kind of capturing, I think your anecdote here. When you start working on something that you see patterns in and then all of a sudden a buzzword, a category emerges that really takes hold. Right. Working on DevOps before there was DevOps probably onto something and maybe giving you a little bit of confidence that you’re heading in the right direction. Let’s open this up to the whole panel. Derek, I see your hands raised. I want to go to actually Heather next only because Heather and I have a long history.
I was CIO when I first met Heather. I think your role, Heather was an account manager for, for an outsourcing company. Outsourcing company. I don’t know what to categorize it. And now here you are running your own executive search company.
And so I wanted to bring you up front because that’s a pretty,
[00:09:42] Speaker D: pretty
[00:09:43] Speaker A: wide leap from where you started from to where you ended up and maybe just share your story behind that.
[00:09:49] Speaker E: Well, I would. Thank you, Isaac. I would suggest it really is not a leap because when you take who you are and be introspective enough to see who you are on the most generic form, I’m inquisitive. And I did research throughout much of my career, secondary research, looking for answers to questions. And in doing so, I had to match what the client was looking for, whether it was an internal or an external client, with a solution. And that’s what recruiting is. It’s finding a match between a candidate and a company and recognizing that the company may not necessarily, your client may not necessarily know what they’re looking for. So being able to interpret that, translate what they’re looking for into a person that meets those needs. And it was that passion for finding answers, being inquisitive, as my husband likes to say, sitting on my ass and talking on the phone and someone is now going to pay me and putting that all together that helped me to launch my recruiting business.
I think the pivotal moment was Covid.
I had been downsized yet again. First time, shame on them. Second time, shame on me and not being prepared.
But when I was taking care of my mother, fortunately she survived. During COVID in Florida, I had a lot of time to think about what is it that I’m good at and what I wanted to do. And I connected with a recruiter for myself and he needed help finding candidates.
And I used that research approach in helping him initially and then taking that as my quote unquote secret sauce for how is not looking at just who has a banner, looking for a job, not going to people that are posting that they’re looking or indeed, where they’re, you know, you can partner with with indeed. But it’s recognizing and really understanding what a client needs and finding characteristics, those characteristics in the people that I might, that I want to propose to them as prospective candidates and using that passive approach.
So to me, anybody that has the skill set that I’m looking for is open game for a conversation.
[00:12:12] Speaker A: I love this idea of taking what you were doing so well as a partner of mine and just waking up one day and saying, I want to keep doing this just in a place that is of greater interest to me and hopefully more lucrative than what you were doing in the past. I just think it’s a great story. We’ve got everybody raising their Hands here to come up and share their stories.
Making the leap to entrepreneur, founder or solopreneur. Derek, what was, what was your spark?
[00:12:43] Speaker F: So my spark was looking at my industry. I started off, you know, pretty much worked with high availability business continuity type systems and some of the larger designs I work with like US Postal Service, some of the government agencies, work with some of the military stuff. And I saw these continuous patterns across where people just weren’t prepared for continuity.
They weren’t prepared for things would happen or go sideways and they say and they would struggle with that. And Covid was a perfect example as many people were caught flat footed because they hadn’t prepared their networks, infrastructure or their business culture to work full time remote. And for me it wasn’t just a one time thing, it was just building process. As Tyler mentioned, the pattern that I could see across the board where these pain points were existing and I always had a passion to say what can I do to help make somebody’s life easier? And because of my background I was asked to evaluate things like the New York Stock Exchange for high availability and other things in continuity. And I thought this pattern. The largest corporation, the last one I worked for was Siemens which was a global company. And I was, because of my background I was put on their special teams. And the special teams meant anything outside the box. So in that case they had a standard product which I helped them further develop and bring out. But the other thing I do is bring this continuity of how could they make things better.
And it just got to the point I said for all the things I’m doing for you guys, I might as well do this for this myself. So I planned a two year exit strategy which means how could I look at and prepare for things like health insurance, putting money in the bank just for what if possibilities and also looking at what are the possible customers I’d be possibly going after that would need these services. And it wasn’t just the small to medium to large business. It was all the businesses across the board that I saw that had these pain points. And by doing this I was able to jump out on a leap of faith. I was able to go in my network and say I’m going to help people develop business continuity or high availability strategies to make this work. And a lot of companies, even to this day I was looking at artificial intelligence. You know, this exists right now. So the aha moment is figure out how do they do this but how do they get people to help them do this? Because a lot of them don’t really have the expertise. And for me, as taking that leap of faith, you know, you mentioned failure earlier.
Early on, I did fail. I did have some companies that I worked with that had contract budget issues that I had to pivot and figure out how to go from working with government entities to now commercial entities. But I was prepared for it because I planned ahead.
One of the things that kind of helped me through my whole process here of entrepreneurship was to establish that resilient mindset. What do I need to do today to prepare me for tomorrow? And that’s looking at the skills, looking at the finances, looking at all the different things that could possibly go sideways, but preparing for them before they happen.
And by doing that, I was able to be resilient in that matter. I did have a customer, one customer I was doing, and I had one client that the budgets had gone sideways. And I pivoted, and they decided they weren’t going to be able to keep me, but they wanted to keep me on as long as possible, and they did. And I pivoted my business. I started working with another company, and they said, you know, we need a CIO and a cyber security officer. Would you be interested in taking this role? And I said, sure.
And I thought I’d be in it for two years. I was there for about six. And after that, I said, time to go back into consulting. So, again, is the thrill of it, the fact that you’re doing things more for yourself on your timeframe, and you get to choose the businesses that you want to work with as opposed to being assigned tasks that may be mundane. And for me, it was the longevity of being able to continue doing what I love to do and doing it the way I want to do it for as long as I want to do it. That was my moment to really kind of branch out and say, I want to continue this, not just for a little bit, but for as long as I can.
[00:16:24] Speaker A: Some really good points here, Derek, that I captured. So I hope others will also comment on. The notion of having a resilient mindset I think is interesting.
I’ve been at it for 10 years.
You know, some folks on listening and speaking have been added a lot longer.
Planning before you leap. That means being prepared in your current job that you might have to or want to be a solopreneur or go off on your own, but then having a plan ready for when you’re doing it and figuring out what some of the elements of that plan, if you, you know, cut the cord or the courts cut on you and now you starting your plan, you’re going to be three to six months out before you have a plan. And that’s, you know, it’s a long time to wait before the, you know, money’s pouring into the door. So I think it’s a good point. And then being able to strateg, I mean, you know, one of the hardest things I will say for me and for all entrepreneurs is picking your battles, picking where you’re going to focus on. I’m terrible at it. And, you know, the client that’s sitting in front of you may be paying you today, but may not be a good strategic path for your future. I’m going to keep going down the room. Thank you, Derek, for the comments. Liz, welcome. Your thoughts on what pushed you to take the leap when you took your leaps on becoming an entrepreneur or founder.
[00:17:54] Speaker G: Excellent. So I’ve been an entrepreneur several times, but I would have to say a huge part of being an entrepreneur is being willing to have that personal sense of ownership over your work.
And not just over your work, but over the old, over the entire process, entire program, entire company. That willingness to think through and have ownership and take ownership and really see the bigger picture, not just the individual tasks that you’re doing. If you already have that kind of mindset, you are an entrepreneur or an intrapreneur or a consultant, however you want to think about it. But taking that core talent and then moving that into generating, you know, making sure that your expertise is valuable opens up so many doors.
And regardless of risk, I want to set risk aside for a second because risk comes in many forms, right? Risk of staying in one place is a risk. Risk of taking a leap is a risk.
So there’s a lot of ways that you can think about risk. And the biggest thing that I would say that I don’t necessarily think that I’ve conquered is that willingness to actually spend time on pipeline and sales.
Both times that I was opened up a new shop for myself, my pipeline and my sales was completely based on my individual talent and my reputation.
And if you think about it, that’s actually the same kind of skill that helps you get a job.
So think about the risk in terms of staying versus leaping, because there really is a, a very similar risk.
[00:19:49] Speaker A: Believe it or not, Liz, that was one of my first realizations that I embraced when I went solo 10 years ago is the notion of giving up the 40 to 60% of my time as an executive.
That was essentially applied to politics, long running, change management, just dealing with enterprise inertia. Or lack thereof, and shifting gears and saying, you know what? I got to sell my own dog food. I got to be able to promote myself.
I got to be able to figure out what sales cycles look like and how to manage a CRM so that it helps manage me. And for those folks who think that winning clients is easy, that is the hardest part of what you’re doing as a founder and as a solopreneur. Hands down, hardest things. Thank you for the comments, Liz. Joanne, you just took the big leap again.
And so I’m really interested in hearing your insights about what was in your mind. From great idea to let’s put time, money, and other people’s lives in the mix of things and make a business out of what you’re doing now.
[00:21:14] Speaker H: Thank you.
I think, I think my turning point was, and I was an advisor for many, many years, whether it was, you know, big consulting firms or in technology companies or manufacturing companies that also spun off technology companies, etc.
So I got to the point of you.
I love being the person that people called when they had a problem and giving them the solution. But it gets to a point where you realize that your solutions and your answers are being taken in. The messages do resonate. People understand where you’re coming from and they adopt your ideas, but then they get lost anyway. I can’t find the right vendor. I don’t know how to.
I want to do exactly what you’re telling us to do, but I. I can’t find the right tools. So I decided that at a certain point, if you have the grit to do it, you kind of put your money where your mouth is and invested not only in my own ideas, but those of other people as well. And we started building the software to solve the problems. And so the turning point, though, was really one specific situation, I guess, where I had been working with this company on and off for more than a year and gave them the ideas, gave them the blueprint, gave them the roadmap to follow. And they did. And they did. And they did. And they failed miserably all the way through. And what I realized was they weren’t considering the tribal knowledge of the people in their workforce, that they were bringing the workforce on too late.
And so that, to me, was the turning point that said you have to build software or tools that people can use to capture some of that, because in manufacturing specifically, 33% of the workforce is going to retire in the next two years.
So you have to be able to give people back something that they can use to Capture all of that knowledge before it rolls out the door. To me, it was a natural marrying process between here’s the solution, here’s the technology, and. And now you have a way of bringing that tribal knowledge into real software. AI gives me the capability to be able to do that. And so we started building the software for that reason, to solve the problems, but also understand that companies need to be resilient and bounce forward and some of that capture of tribal knowledge helps them do that.
[00:23:51] Speaker A: Joanne, something you mentioned. I’m just going to share for everybody listening, there are a couple of good books I’ve read about being able to pivot from a consulting practice. One, having one or two clients that you’re working with and basically using it to feed the bills, but stealing your time from your ability to build a scalable solution and product and making that leap over from service company to product company.
Interesting to you? If you’re challenged by that, leave me a message here in the comment stream. I don’t have the books handling, but I do have a couple really good books to recommend on this. And it isn’t an easy pivot as it sounds, folks, let’s move on to Martin.
Martin, your thoughts on your pivots and shifts to solopreneur.
[00:24:45] Speaker D: So my pivot was really about a choice. It was about a choice of do I look for another company to work full time or do I look for an opportunity to just consult on my own basis?
So I chose to go that consulting route about. I think it was about five or six years ago now.
And I think the.
There’s some key things you have to remember about going out on your own. Like that.
[00:25:18] Speaker A: That.
[00:25:18] Speaker D: Yeah, and the first one is, well, who’s going to employ you? You know, who’s going to employ your company, you to do consulting for them. And if you think you’re going to do that instead of looking for a job and all the thing about trying to get an interview, all that type of stuff, it’s kind of the same problem because unless you’ve actually got a good network, you’ve got people who trust you, that know you, that can help you find your next customer, it’s pretty much the same as trying to find a job and getting an interview. You need that network and it’s so important. Yeah, if I look at the work I’ve done, the majority of it has come through actually somebody who knew me that happens to be at that company, etc. Etc. Or knew somebody that knows me or whatever else. So it’s that personal connection so that piece is absolutely critical. So don’t think you’re getting away from that by not looking for a job because you’ve got the same problem.
And I think there’s a couple of kind of key learnings that I would share.
One is that your attitude to who you are changes.
So, yeah, previously my attitude was I’m a cio, I work for Company X. So I am the CIO for Company X.
That is my identity.
And yeah, Heather will talk about this, about personal branding and things like this.
As an entrepreneur, as a consultant, do your own thing. You are managing partner of a consulting company or whatever else. So you, you have to actually define your identity differently. And that’s a very big mental adjustment if you’ve, especially if you work for one company for many, many years or something like that. It’s a very big mental adjustment that I am me, I am not a factor of this company.
And that’s so key to actually identify who you are and what you are going to sell in terms of selling yourself, selling your capabilities and things like that.
And then the third thing I was going to mention, sorry, no bar.
[00:27:27] Speaker A: I’m capturing this because every one of your comments is exactly what I found I felt in my first couple of years of going solo and I was solo before I really started star cio.
So I felt all those things. I was like, gosh, I wish there was a coffee with digital trailblazers 10 years ago explaining this to me.
[00:27:50] Speaker B: Yeah.
[00:27:50] Speaker D: So the third thing I will share is your different mindset between I’ll call it being a wage slave and being an entrepreneur.
So being a wage slave, yeah, you’ve got the nine till five, you’ve got vacations that you. So many days of vacation you’re allowed and you have to book them. Everything else, if you’re running your own business and doing this, there are, especially if you’re doing consulting, you have two types of hours. You have hours you’re getting paid and hours you don’t have. Don’t have pay.
That is it hours. Are you getting paid now as you’re not getting paid, there is nothing else. Doesn’t matter if it’s a weekend, it’s a holiday, it’s an evening, or whether whatever else you have, hours you get paid and hours you don’t get paid. It gives you more flexibility so that you can go and do things during the day if you want to. Whatever else, you just have to make sure you organize yourself a little differently. So there is a big mindset change in a couple of areas there’s I
[00:28:53] Speaker A: call it sweat labor. I think the industry calls it sweat labor.
Martin and what you don’t realize is when you start out early, that sweat labor can be relatively small. You know, you got to incorporate, get a bank account, maybe put a website up, you know, update your LinkedIn page and, you know, some overhead to just get getting started. But as you’re going on and when you think beyond just pipeline that Liz mentioned and saying what it takes to run even a small business, it adds up quite a bit. And your to do list never ends. And that’s why a lot of solopreneurs are always stressing and always putting more hours than they really should be, because that’s the nature of the work and you have to manage it. John, I want to get your insights before we go to the break.
You, like Liz, made a sizable pivot in what you’re doing. I wouldn’t even know. I don’t even call what you’re doing a pivot. I’m going to use a word later on. I don’t want to use the word yet, but tell everybody what your mindset was and tell everybody what you’re doing.
[00:30:02] Speaker I: Yeah. Isaac, thank you for having me on.
My career really started by building products and systems and teams at product companies, and I was at a lot of other high tech companies and I was in Consulting for 10 years and I really enjoyed that. So I did that stuff for 20 years and just had a really, really good time. And I was talking to some friends that kind of actually made a pivot out of that type of work. And the reason that they were doing it were for the reasons that people described. One of the additional reasons is that I wanted to spend a lot more time in the community.
For the last 10 years, I had spent so much time kind of on zoom calls talking to people that I really wanted to spend more time.
And so my friend and I, we were looking at what kind of things would be really fun to do, and we decided on running local service companies.
And so the first thing we had to do is try to figure out what kind of local service company do we want to run. And so we looked at all sorts of them. And the one that looked like it would be really, really fun and needed in the community was actually to provide basically send nursing assistants out to people to help them age in their house.
My friend actually he went to the route of buying one of these and he bought ultimately three of them. And he’s running the AT scale.
And my wife and I were interested in buying one. But we just, we didn’t see one in our community and we didn’t see anything that we want. And so my wife was the one that really said, you know what? You should build this thing from scratch. And we got, actually, we were thinking about that, but then we actually also bought into a franchise system which, which helped and made it easier. And so what we do is we have what’s called an in home care company that we’ve started in local, in our community.
And we basically help people age at home. And it’s been such a rewarding experience.
It’s something like every day I’m often able to just meet people and help them get out of the hospital or help them get out of a rehab center and through providing nurses assistance out to their house, make their life better so they can have more rewarding time with, with, with, with their, their family members as they’re aging. And so that’s what I’ve been working on. And I’ve learned so much about running a business and all the different parts of it. And the part that really surprised me was how much technology you need to run these things. And, and then the other part is how much fun it has been to work with the other owners that have these things and collaborate on trying to make things better and collaborate on like putting on webinars for things and improving our CRM system and our other systems and security.
And so that’s, that’s what I’ve been working on. I’ve absolutely loved it. Never anybody ever wants to talk about this stuff. Just reach out, because I’d love to talk about it.
[00:32:42] Speaker A: Hey, John, there’s a couple of articles when I was doing the research about just the amount of technology and now AI being applied in small business again.
If anybody wants that research, I’m going to paste the links in for what I have posted already later. But I do have some really good research on how small businesses are thinking about AI. John, after the break, I want to come back to you. I want you to hear just sort of the emotional level, like you really left your old world. This is not you. You know, you kind of like, you know, said, I’m gonna go do something completely different.
And I just wanted to, you know, like, kind of magnify what was going through your head at the time. Because it wasn’t like you didn’t like what you were doing before, was it?
[00:33:29] Speaker I: Yeah, yeah, no, I, I like what I was doing. I just, I wanted a different experience and I wanted to spend more time with, with people in the community.
And then I wanted to see if I could build a local business up from scratch.
[00:33:41] Speaker A: So it was the challenge. There you go, folks. This is what we’re talking about today. The challenge of National Entrepreneur Week. The opportunities for digital trailblazers to either go solo, become a freelancer, join a startup, become a founder in all of its different flavors, not just from a business perspective.
John is talking about a complete lifestyle and career change, industry change, lots of things that you have to be brave around.
There’s some risk, it requires some resiliency, as Derek pointed out, and it requires the ability to experiment. There’s a couple questions and comments on the stream. I hope you’ll leave some around. The ability to experiment your first ideas, even when you have a plan, requires testing that market fit. Learning from what’s working, what’s not working, and deciding, hey, am I heading in the right direction? Folks, thank you for joining this week’s coffee with digital Trailblazers. I am ready to start announcing our March episodes before we get there.
Next week on the 27th we’ll be talking about DevOps in the AI era, restating QA’s mission. I think I have a special guest lined up for that one, so if you are in technology, you don’t want to miss that one on the sixth. Elena, this was your idea. I know you’re listening. I hope you have the sixth free to talk about rethinking KPIs for the AI era, how senior leaders prove business value. And you wanted to talk about cross functional business values. I think we’ll have Elena back. Hopefully she is free on the 6th to join us on the 13th. This was another thing that came up. I think it was last week and we always talk about whether somebody is a cultural fit for your organization or a partner is a cultural fit for your organization. And culture fit is one of these fuzzy gray type of squishy words. I think we’re going to put some concrete definition about how we talk, measure, evaluate culture fit. That will be on the 13th. On the 20th we’re going to talk about managing AI agents. This again came up last week. This notion that teams are not just people, they’re people and agents, that leaders and managers are not just overseeing, partnering and collaborating with people, they’re doing it with people and AI agents. And we’re going to unpack what managing an AI agent is on the 20th and then the 27th. I’m glad sales came up. Up. I’m glad marketing came up.
Liz brought this up a couple weeks ago And I said, you know what? We’re going to need to talk about the essential sales and marketing skills for digital trailblazers. Not only if you are going off on your own, but I talk about this in my book, Digital Trailblazer. If you want to make sure you get funding and traction with your big ideas, whether you’re separate and running things on your own or a founder or inside a company, you better be able to have the skills to market and sell it. Folks, starcio.com Coffee will always redirect you to the next episode, but do visit this page drive starcio.com Coffee and that is the coffee page where you will see the episodes that I’ve published. If you missed an episode, you also have a link there called add to calendar. Put it directly on your calendar so that you will not miss a live episode when you can make it. Folks, I thoroughly enjoy working with you here and thank all my speakers for being here with us. Folks, we’re back. Tyler, bring you Back to talk. Two things for the remaining 20 minutes that we have. First, I want to talk about your lessons around resilience, risk and experimentation. And then your thoughts on the future. Right. Looking ahead, how do you see the next wave of digital entrepreneurs shaping industries or community?
Tyler, your thoughts on either of those two areas?
[00:37:53] Speaker C: Yeah, absolutely.
I, I dropped a comment where I said that I wish I’d understood earlier about entrepreneurship that it’s, you know, grit is a, you know, table stakes. But what it’s really about is humility and energy management. You know, looking at the, the high levels of stress that we deal with, having to carry so much on your shoulders as an entrepreneur, you know, when you spent decades building expertise as, as most of the folks on the panel have especially complex systems, you know, you, you develop conviction. You, you see this, the flaws, you know what’s broken.
You know that experience is powerful, but it’s also dangerous.
A lot of experienced leaders who become entrepreneurs, you know, we assume because we understand the problem, we understand what the market will fund, but we don’t. Markets don’t reward being right or, you know, they were. They reward pain, solving for pain. They fund firefighters before they fund fire proofing is another way to say it. You know, you can design something that makes the system work the way that it always should have, but there isn’t visible pain.
Nobody’s going to pay for it. So you have to listen, you have to understand what people are actually afraid of, what keeps them up at night, what their incentives are, not what the system needs. Over the next five years to innovate that the energy management side is. It’s just as real. Inside a corporation, there’s inertia, outside there’s none. Every day requires activation energy.
Nobody’s looking over your shoulder.
Resilience. It’s not pushing harder, it’s managing your energy, separating insight from ego, choosing a wedge that aligns innovation and structural truth with urgent pain.
And you have the experience, so that gives you the pattern recognition.
But the entrepreneurship piece forces you to translate it to something that the market feels today. And just real quickly about the next wave. I think the next wave of digital entrepreneurs are going to be the ones that can bridge that structural optimization things like DevOps that we mentioned with solving that acute pain. So bridging that gap.
[00:40:32] Speaker A: Tyler, you’re reminding me again of some books I read. I read a lot of marketing and sales books, a lot of wisdom in that area that are outside of my primary skill sets. And you know, listening for pain points is a really important skills, but it’s not sufficient. You have to look for things people actually pay for. And if you’re listening and you’re thinking about going off on your own, let’s make sure that you’re actually building a sound business. And if you need those books, do put a comment here. I will share the links to them here on the comment stream. I’d love to hear who else is thinking about going solo. Derek, hold off a second. We have not heard from Joe today. I see his hand raised all the way at the back of the line. I want to bring him up to the front of the line before we run out of time. Joe, do you want to talk about resilient risk, experimentation or the next wave of opportunities?
[00:41:30] Speaker B: So I want to talk about motivation and risk and I want to talk about how the world has changed over time.
When I was a young whippersnapper, I was motivated. I was all fired up. You know, I always talk about fire in the eyes and fire in the belly. I really wanted to conquer the world and I was working for a big corporation as an associate programmer and I was told that the, the track for advancement was, was something like five years, which to me was an eternity.
I was risk tolerant, you know, just full of vim and vigor. And someone offered me an opportunity to take part in a small startup, a little, what we would call bi today, a little bi firm. And two years into it, three years into it, I was a partner and I learned a very valuable lesson. And I think it’s already been mentioned here, you don’t Eat. If you don’t hunt, you got to close the deal. And I can tell you stories about some interesting meetings where I had to ask for the order to get, to get the contract signed. You know, a little bit later on in life you become a little more risk averse when you have a mortgage and you have kids and when, when the circumstances are a little different, you worry about your next job.
And as you know, I counsel people in the MIT program about the importance of networking. And Martin, you, you hit the nail on the head. Your network is just so, so important.
So I set up an LLC between jobs and made sure that I had interim work and that I stayed in touch with my network and that I always looked like I was busy and engaged because I was.
Now a little later in life, I’m financially stable, I’m risk tolerant, highly risk tolerant, and I was offered an opportunity by a good friend to collaborate on 10x NewCo and help companies to design their growth strategies and leverage technology.
And I have enough background and experience to be able to do that.
Not interested in a full time job, but happy to help companies whether it’s on a paid or, or even a, you know, all the board work that I do, which is pro bono.
So the point being, I, I think there’s, you know, there’s a, there’s opportunity, there’s motivation and there’s risk tolerance that are all factors here in, in the continuous.
[00:44:10] Speaker A: Joe, thank you for that. First is like, I love connecting Tyler’s thought and yours. You know, if you don’t have that fire in the belly, it’s really hard to be going off on your own or being in a startup. If you do, you need that grit.
As Tyler said, that’s table stakes because chances are you’re not going to be anthropic or open AI and strike it rich. Even though, you know, it took a bunch of years of people putting a lot of sweat labor in for them to get to where they are right now. And then something you see a lot on the technology side again from Tyler’s comments. Being able to manage your energy, that’s not just about a mental health question. It’s about being able to take a step back and do that. Listening. I forget who said being able to listen for the market.
If all you’re doing is driving faster, faster, faster, release, release, release. It’s, you know, you’re just pursuing the next thing that you have right near in your headlights. You’re not necessarily being strategic. Got a bunch of hands raising here. Let’s go around the room. Derek, your thoughts on opportunities, resilience, risk and experimentation?
[00:45:21] Speaker F: Yeah, so I think from the resilience point of view is looking at resilience.
It’s not about avoiding failure, but it’s really looking at how you can survive learning cycles and challenges. Those are the kind of things that people need to understand. And the things that Tyler mentioned and Joanne, those are all spot on because it’s a learning process. And I think some people, they just need to understand. When you’re stepping out there, what exactly are you going to do? Is, as Martin mentioned earlier, identifying your brand earlier and identifying exactly what you can do and do better will help differentiate you from the rest of the people that are out there. Because if you look at it, there’s going to be risk involved, but risk is cumulative. It’s not just isolated to certain things. You depending on where you live, the market you’re trying to penetrate, the culture, the community, all these things come into play. And understanding that risk early on is going to help you. You figure out what you need to do and how you can do it within your realm. You mentioned, it was mentioned about experimentation earlier.
These are kind of things when, you know, as Joe mentioned, you know, you’ve got the fire in your belly and you’re ready to take on the world, but you have to be realistic. You know, everybody wants to do as much as they can, as fast as they can, but reality is you need to set up guardrails as you’re experimenting to figure out what’s going to be the niche for you. You can move fast if you have a blast radius, but otherwise you can’t boil the ocean. And these are kind of things. You go out there, you experiment, and you try one thing, it doesn’t work, and you figure out, how can I pivot to make that better? These are the kind of things that help develop that resilient mindset. And Joanne brought up a point about the people in the organization, which I thought was very key. The people are another factor. The people you interact with is going to matter. The people you communicate with, the people you trust, the psychology, the safety, determining how are you going to move these things forward. That’s going to help you get your business and your brand out there. That’s going to be a key focus to help you really kind of navigate that area, because it’s going to be highs and lows. And as we’ve all experienced on this call, there’s going to be failures. But how do you address those?
How do you get through those challenges? Endure those struggles. When I look at it from the resilience point of view and the mindset, resilience is something, a resilient mindset is something that’s developed during calm periods, but it’s revealed during times of stress and challenges.
And I think the preparation and the work you put into it beforehand is really going to tell how you can work from those lessons learned from things that other people have done and apply that to your particular mindset in your business and to see how you can do it better so you can avoid those potholes when you move it out in the business that you want to pursue.
[00:47:47] Speaker A: You know Derek, there’s a few people here that manage the importance of having connections. I think what’s maybe even more important is having honest advisors, right? That you can make sure that you’re comfortable sharing something well before you’re ready to go to market or put your time and money into things and get real honest feedback. Hey, is this a bad idea?
And I just think it’s so important, Liz, where you want to go. Resilience, risk experimentation or next wave of opportunities for 500.
[00:48:23] Speaker G: I want to build on your concept of having advisors because this kind of goes back to the whole concept of making sure that you have the right level of support as you move into being an entrepreneur.
Someone once told me that you should assemble a board for your company and whether they know that they’re on the board or not is immaterial. But think through how you’re going to get that those different aspects of a company, if you’re thinking as a company to who’s going to be able, the right person to talk to about that sales pipeline? Who’s going to be the right person to talk to about your product delivery? Who’s going to be the right person to talk to even about infrastructure or your admin. Right. Putting that, assembling that right set of support as well as you know, for your mental and physical well being is absolutely 100% critical. One thing we didn’t talk about at all was healthcare.
And as an entrepreneur, healthcare is the number one, the number one expense.
Unless I mean, unless you’re actually investing in technology, etc. But healthcare is huge and having that, having a spouse or some other way that you can, can source decent healthcare is a big step up in terms of making sure that you are supported in your endeavor.
[00:49:50] Speaker A: Yeah, I’m really glad you brought this up.
It is probably one of my mistakes is not looking at my 10 year horizon with kids about to go into college and finances are tough I mean, you have some strong years, you have some weak years. That’s the nature of business this. But being a solopreneur has gotten extremely expensive over the last few years, primarily driven by healthcare. And you need to understand those financial risks and realities before you take that big leap. Thank you for bringing that up. Who’s next? Joanne, welcome back.
[00:50:32] Speaker H: Thank you.
I think I want to talk in all three categories at the same time, if that’s possible from a resilience and risk and experimentation perspective.
I think the one thing that I would say to new entrepreneur people who are going to, you know, jump on the AI bandwagon or the next iteration of new technology, maybe quantum or whatever, is it’s about business value.
And, you know, we all go through this. Who am I going to sell to and how am I going to leverage my network and whatever. I would say the better piece of advice might be, it’s just a personal perspective is how have you walked in the shoes of the person you’re selling to?
And it’s not about applying your expertise necessarily, it’s about connecting with them, not only where their pain is, but where they’re going to have to take their journey. And that business value, I think, is the thing you have to experiment with more than even the product.
Because the product market fit is one thing. That’s what will the market bear in terms of cost. But more importantly, it’s how are you making people’s lives better, even in the most insignificant of ways, if you’re giving them back time, if you know their political struggles in a large corporation, if you understand the value that you’re creating for them and then inculcate that value into a product, you’re that much farther ahead. You know, one of the first things that we did from an experimental point of view was what are the key challenges across all the different sectors of manufacturing and what are the commonalities across those? And you, if you can boil the ocean down to five or six main things, you have a product roadmap and you have a way to build because you walked in someone else’s shoes and you are going to be walking in their shoes going, going forward.
[00:52:27] Speaker A: Talk about being customer driven from the early stages.
You know, I am. If you’ve walked in their shoes, you got a leg up on everybody else. Thank you, Joanne. Heather, what’s up?
[00:52:39] Speaker E: Thank you. For me, risk or experimentation was actually the same thing. Being able to take that risk and experiment with another organization, that would help me. And I think the focus on the human touch is what I would use as the third topic you have and what is the next wave of digital entrepreneurs need? And no matter what the technology is, no matter what your area of focus is, don’t forget that people are involved, that you can use the help from people, and that the human touch is going to be critical. And for me, being able to take that leap and asking for help and knowing who to ask or finding out who to ask sometimes by chance, or taking that risk and saying maybe this person can help was very valuable to me.
[00:53:28] Speaker A: Thank you, Heather. And just full disclosure, just before this call, I said to Heather, I need a half an hour of your time. I need some help knowing who to ask and when you need some help. Thank you, Heather.
John, final thoughts today.
[00:53:44] Speaker I: When I was thinking about doing this, I did all the same stuff that I did at product companies for products, and I looked at like, you know, is, is this needed? Right? And, and I was really just like wrapping my head around the axle and, and actually I had a really nice conversation with my brother and my, and my, my brother’s like, look, if you know that the business model works and, and you know that there’s customers out there, at some point you just, you got to go for it. And, and, and that’s, that’s was really the turning point for me. And I just thought that, you know what, I could either probably work in the tech companies for, for 10 more years, or I could probably do this for 20 more years.
Kind of, it’s, you know, like, it’s a little bit of a grind, but like, once it gets going, you know, like, this is something that, that I can probably just, you know, as I age, it would be something that, that’s fun to do. And then I did have the personal experience when, when I was 16, my grandma got too old to move, move and live by herself, and so she moved into our house. And then my mom has had serious dementia for the last six years, and my brother’s had to take a lot of time off work to basically help my parents out. And so we knew that the business model was there, we knew that the customers are there. We live in Seattle. And we ultimately decided that I wasn’t going to be happy if I didn’t take this when I knew it would work. I wouldn’t be happy later. And so just for myself, I had to go build this thing, otherwise I was going to regret it in the future.
[00:55:07] Speaker A: Thank you for sharing that, John. Right. Pick. Figuring out your timing is more than just a financial.
[00:55:15] Speaker I: Yeah.
And, and I just, I was starting to see how hard it was to be older in tech. And I probably shouldn’t say that, but it’s, it’s like a real thing. I was having founders ask if I was. I, you know, they were asking the employees, hey, is that guy too old to be in tech? And I’m like, oh, oh, that’s, that’s a real thing.
[00:55:31] Speaker A: Holy cow. We need to have this conversation in a future digital trailblazers coffee hour. Martin, final thoughts today.
[00:55:39] Speaker D: I’ve got two thoughts, both related to balance. And we talked about this a bit earlier is when you’re an entrepreneur, he’s making sure balance your time for yourself and your time for family and things like that versus work. Yeah, I talked about hours, working hours or I was paid and I was not paid. You’ve got a balance. You could work every hour and still.
[00:56:01] Speaker A: Yeah.
[00:56:01] Speaker D: And kill yourself.
[00:56:03] Speaker A: Yeah.
[00:56:03] Speaker D: Mentally or whatever else. So balance in terms of work and non work and the other is balanced diversification.
So don’t put all your eggs in one basket. Obviously you’ve got to be careful not over stretching yourself and making sure you try to do too much, but balance diversification. So for example, from my service consult consultant, I do some consulting work on projects for people. I do some consulting work in terms of mentoring and coaching of senior leadership and I do some assessments as well. So balance diversification and balance of work and non work.
[00:56:42] Speaker A: Thank you, Martin, for joining. We’ve got three minutes. Go ahead, Liz.
[00:56:49] Speaker G: I was going to speak about the whole idea of making sure you’re on track with your clients.
And I have an image and I put it in the, in the chat. I have this image of one of the most successful entrepreneurs I ever worked with who would talk about making sure you’re getting on the right wavelength. This goes back to listening skills and making sure that you’re able to modulate to the person’s wavelength wherever they are. I think that Joanne touched upon this. Making sure that you’re able to relate that you’ve walked in their shoes and really identify with them and sort of merge with them and that once you have that sort of symbiosis, that’s when you can actually start modulating them up in a way.
I can tell you that I fall, speaking of test and learn, I’ve fallen on my face a couple of times where I just want to come out with people. I’m like, like it’s completely obvious this is the answer. I can be your everything for you, blah, blah, blah, blah, blah. And they look at you like you have six heads because sure, that might be the right answer.
They’re just not necessarily ready to hear it that way.
So making sure that you’re able to modulate to your client and your customer, critical for success.
[00:58:04] Speaker A: Thank you, Liz, for joining this week. Tyler and Joanne, we’ve got two minutes.
[00:58:10] Speaker C: Yeah. So I just wanted to share a framework I created for selection of a market or a beachhead as an entrepreneur.
So there’s eight elements. There’s a ninth that I’m not going to share that you’ll have to reach out to me if you want to hear it. But pain is real and recognized.
There’s a potential for a strong executive support, the presence of underutilized and unrealized economic value leadership’s actively trying to unlock. The buying group is defined and manageable. The first deployment can be clearly scoped. The first outcome is measurable in business terms.
The market scenario combination is structurally sound. And the business scenario is not easily solved by pre existing incumbent solutions.
[00:59:02] Speaker A: Wow, that’s a, you know, shave $100,000 or more off a McKinsey or other Big Six consulting firm to help you figure out your go to market strategy for your startup. Thank you for sharing that, Tyler, Joanne, last word.
[00:59:22] Speaker H: Last word. Make sure that you diversify your network to be inclusive of, excuse me, of not just leaders, but people below them, those that are aspiring digital trailblazers. Yes, a startup advisory board is great, but you need to populate it with people from all different aspects of the career path, not always the cio, people who work below them. Directors go all the way down into the workforce because that way you get the perspective of, of all the people who will be involved in using your product or choosing your product.
[01:00:00] Speaker A: Thank you, Joanne, for those final words. Tyler, for your framework and joining us special this week, everyone else for your insights on what it’s like being a digital trailblazer and going off on your own, either as a solopreneur, as a freelancer, as starting your own startup, or joining a startup. What a great conversation here.
This one will be released publicly, so if you missed it, you can find it on Apple.
You’ll be able to find it on Spotify, on LinkedIn, and on my blog, which is drive.starcio.com Speaking of my blog and speaking of Joe’s recommendation, learn how to ask for the order. I’m not asking for an order, but there are 27 people still listening here, folks. If you have not signed up for my newsletter, please do so. It’s free, it’s once per month.
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You’ll also get benefits for being able to join the community.
And you’re going to hear about some of my special projects where I will be at specific conferences and hope to meet you at one of them. If you’re going to be at Adobe, at SAP, at Appian, at Atlassian, those are just conferences that I’ll be over the next few nights. Nutanix I’m probably forgetting a few in there. It’s going to be a busy couple months of travel. Folks, thank you for joining this week’s Coffee World Digital Trailblazers. We’ll be back next week to talk about DevOps in the AI era. The six about rethinking KPIs for the AI era the 13th around culture fit March 20th around managing AI agents and on the 27th around sales and marketing skills for Digital Trailblazers. Folks, thanks for joining. Have a wonderful weekend. See you next week.
