Paul Dorney

Bio

Paul Dorney is a founder/CTO originally from Cork, Ireland, now living in Charleston. He’s built and scaled companies across fintech, sports tech, and prop tech—including the largest gig-economy platform for sports officials in the US—before moving into ed tech. Today he’s applying AI to transform higher education and fundraising at Gravyty, helping mission-driven organizations connect, grow, and thrive in entirely new ways.

Summary

Paul Dorney has significantly transformed the landscape of several industries through his entrepreneurial endeavors, particularly as the co-founder of Silbo, a platform designed to democratize youth sports officiating. In this conversation with Jothy Rosenberg, Paul elucidates his journey from a secure position at SAS to the challenging yet rewarding world of startups, emphasizing that the most pivotal decision for founders often lies in the strategic choice to decline opportunities that may stretch their resources too thin. He shares invaluable insights on the necessity of building cohesive teams, akin to a band where each member brings unique strengths to the table, rather than an interchangeable orchestra. Furthermore, Paul candidly reflects on the misconceptions surrounding product superiority in the startup realm, asserting that effective marketing and sales strategies are equally critical to success. This episode encapsulates the essence of startup reality, underscoring the importance of resilience, adaptability, and the relentless pursuit of growth amidst challenges.

Notes

The conversation unfolds with the introduction of Paul Dorney, a distinguished entrepreneur whose ventures span diverse technological realms, including youth sports officiating, home inspections, and educational chatbots. Dorney recounts the genesis of his startup journey, originating from Cork, Ireland, and transitioning to Charleston, South Carolina. Notably, he elucidates the formation of Silbo, an innovative platform likened to Uber for youth sports officials. This venture emerged from a keen observation of the systemic issues plaguing youth sports officiating, leading to an endeavor aimed at democratizing access to officiating opportunities for aspiring referees. Dorney candidly shares the tribulations faced during Silbo's inception, emphasizing the crucial lesson that sometimes, the most prudent business decision is to decline opportunities that could jeopardize the operational integrity of the startup. He reflects on his evolution from a technical founder into a multifaceted entrepreneur adept at navigating the complexities of startup dynamics and team management, providing invaluable insights for both budding and seasoned entrepreneurs alike.

Takeaways

1. Paul Dorney emphasizes the critical importance of strategic decision-making, particularly the necessity of sometimes saying no to opportunities that may overextend a startup's resources.
2. The notion that having the best product guarantees success is a misconception; effective marketing and sales strategies are equally vital for achieving market traction.
3. Building a cohesive team is essential; Paul likens his successful startup teams to bands, where each member contributes unique and complementary skills rather than interchangeable capabilities.
4. A significant learning experience for Paul was navigating the complexities of startup growth, particularly the logistical challenges and the need for adaptability in operational strategies.
5. Paul advises aspiring founders to focus on building trust within their teams, as this foundation is crucial for navigating the tumultuous startup journey together.
6. Continuous education, particularly in areas like venture capital and market dynamics, is essential for technical founders seeking to broaden their entrepreneurial acumen and effectiveness.

• Gravyty | AI-powered engagement & fundraising for higher ed
• LinkedIn
• X/Twitter
• Who Says You Can't Startup | Full Bundle | Incorrigible Entrepreneur - Jothy's four courses for startup founders called Who Says You Can't Startup!
• Jothy's TEDx talk - On why those with disabilities tend to overachieve
• Our YouTube channel
• Designing Successful Startups — Jothy Rosenberg | Author | Speaker | Podcaster - Site with all podcasts
• Tech Startup Toolkit book
• Please leave us a review

Hello. Please meet today's guest, Paul Dorney.

The original team has come with me each time because we built that camaraderie together. Like we, we know who has gaps where, how we work well together.

And my other thing is like, educate yourself, especially if you're the technical side, educate yourself to get more well rounded.

What do youth sports officials, home inspections, and college chatbots have in common? They're all industries that Paul Dorney has revolutionized through his serial founder journey.

From Cork, Ireland to Charleston, South Carolina, Paul has built and exited companies in three completely different tech sectors. And he's got the battle scars and wisdom to prove it.

In this episode, you'll hear how Paul left the comfort and piano music of SAS headquarters to co found Silbo, the Uber for youth sports officials and nearly missed filing a critical 83B election.

With just 48 hours to spare, we'll dive into his biggest startup revelation that sometimes saying no is the most important business decision you can make, especially when you're tempted to expand too quickly. But what makes Paul's story compelling isn't just the three successful exits.

It's his brutal honesty about the preconceptions that almost killed his companies from believing if you build it, they will come to learning that the best product doesn't always win.

Paul shares the hard earned lessons that transformed him from a technical founder into a serial entrepreneur who now leads teams through complex mergers and integrations. This is startup reality without the Silicon Valley fairytales. And here's Paul. Welcome to the podcast.

Hey, nice to meet you. Looking forward to chatting and thanks for having me on.

Absolutely.

Well, Paul, I think just with the short sentence you said, people are going to be able to guess the answer to this next question, which is where are you originally from and where do you live now?

Yeah, well, probably not as lot of us here, but I'm originally from Ireland, from Cork, so always Cork first, Ireland second for Cork folks. And I live in South Carolina, so Charleston, right down by the water. So it's, it's a rare mix.

There is a, another Irish lad I live, who works with me who lives nearby. So I think we're the two Irish folks that live here.

We've ran into one or two, but it's, it's definitely a rarer occurrence than previously when I lived in Boston, where, where a dime a dozen.

Yeah, they're. They're a dime a dozen. All the cops are Irish.

Yeah. If I say y', all, y' all is the one that, as I've been told, that that gives you. The Southern. The Southernness, basically, if I keep saying y', all.

That's right.

Once, basically. So it hasn't stuck yet.

Okay, so we're going to talk a lot about startups and the different industries you. You've been in, but if we go back a little ways, you worked at a, at a big company.

So SAS is the name of the company that's the one that's in Cary, North Carolina, right?

Yeah, that's. That's correct. It's got the. The giant business park in Cary, North Carolina.

It's like, I think it always ends up in like one or two of best places to work in the US and super unique kind of area where on site they have like a hairdresser's, a doctor's office, two gyms, soccer fields, baseball fields, everything. Any. Anything you need is cool.

And then been on that campus many times. And by the way, when you go to lunch, there's. There's pianists that play music at lunch.

That was the, the strangest one. The first day I went for lunch, I was like, what is cool? I just thought it was like a colleague who just enjoyed the piano.

And then it's like, oh, no, that's. They have that every day. So a pianist playing every day and you're like, whoa, that's wild.

And then I think the claim to fame is Iron Man 3, that they used it for Tony Stark's offices. So that gives you an idea of how snazzy the newest buildings are.

Those were snazzy looking offices in the movie. So. Yeah. So you left there. You know, it's funny, I.

Yeah.

You'd been there for a while.

Yeah.

Were you literally there on site or were you working remotely?

Before you look and see, can I build a company myself with my, with two of my friends. It's a really cool experience because at SaaS we got to build like a really impactful product that got great traction, all that stuff.

And in my head I was always like, oh, I wonder, could I do this without the safety nets if that makes sense.

Which sounds strange, but basically at the time, you know, one of my friends had noticed that youth sports officials, he was always like, where do they come from? And as he dug into it, he realized there was a lot of parallels between the taxi industry with the dispatch systems, etc, like that and Uber.

And the idea is there that you would, we would bring qualified sports officials onto the platform, folks who are interested in becoming sports officials, and we could get them trained up and then we could go to tournaments, leagues, cities, and they could upload their schedules and geographical based in your area. You could see games that you're qualified to work.

So the key being the qualified, if you were a certain level of like the US Soccer referee, you saw certain games, et cetera, like that. So then you could go check in or reserve the game, check in, check out, get paid. It's kind of similar to like your any other gig economy workspace.

So really cool, really cool kind of experience there.

Because what we had noticed is, you know, you read the news and it says that there's a shortage of officials, which there is, that you could always do it more. But a lot of it was the segmentation. They kind of work for specific organizations.

Whereas what we were trying to do is democratize it, create that open platform where you could work where you want, when you want and that they were in control of their schedules versus being sent to different locations. Really cool. I owned technology there was.

We expanded to 14 different markets, ran it for four years, learned a lot about baseball that I did not have a clue about as well. And a lot of different sports. I became a sports official as well.

Really cool experience.

You just called it soccer. So you've been.

It's funny in. Because my cousins in England killed me for that. But in Ireland a lot of. Because we have our own sport called Gaelic football.

So growing up, a lot of times we call it soccer because we call football Gaelic football too. So it's kind of funny that they give Americans a lot of hard time for call it soccer, whereas we kind of call it soccer as well.

That's so funny. I had no idea that there was a Gaelic football.

Yeah, Gaelic football, yeah, it's super fun. Gaelic football and hurling are kind of the national sports of Ireland. They're amateur based, but they're, they're, they're interesting.

They actually, actually play. It's in Canton, up in Boston and stuff like that. And there's, there's teams all around the country.

I joke that the, the Gaelic association of Ireland. I joke that they run the world. You could go, you can go to anywhere in the world and there'll be like a local team and people playing.

So it's a lot of fun.

Well, knowing the Irish, I assume it's a brutal sport.

It's. Yeah, it is, it is a lot of running. I can't say it, I would not be able to play it my, my current age.

But when you're younger it gets you super fit and then a lot of fun. Obviously the apres games basically is always a lot of fun. So.

Okay, so what was the, I mean, was everything peaches and cream in that, that company was called Silbo.

Yeah, yeah. Spanish for.

Was everything peaches and everything peaches and cream? If not, what went wrong?

No, no, it was definitely, definitely a great learning experience. Like a lot of stuff.

You know, we went into a bright eyed, bushy tail thinking like, hey, we're gonna, we're gonna change everything, if that makes sense. But like a lot of different, a lot of different challenges to solve.

And because we were basically in where, you know, it was, we had to get someone from A to B on a certain time. And that comes with its own logistical challenges. Challenges. So on the technology side, that's a fun challenge.

You know, how can we implement like alerting systems and et cetera, what third party services can we use? But on the people side, you know, the gig economy space, you're like.

And it doesn't matter if it was youth sports or like food delivery or everything that you're dealing with, people, you know, and then it's a Matter of how can you empower them to leverage your tools to get to where they need to get to, but also then keep your customers happy?

You know, are they getting updated on time, how do you handle no shows, all that sort of stuff on the technology and delivery side, but then on the business side too, it's because, you know, it doesn't matter if our product's the best out there or what it is, is like, do we have our sales and marketing lockdown when we go in front of these leagues, can we deliver what we promise? And stuff like that.

So some of our biggest challenges, I think was we made some mistakes that like, I think every startup does is we got interest from a few different cities, our towns and tournaments, and we were like, we have to take it, we have to take it. You know, some of the biggest lessons I learned doing it is sometimes no is the right actual business decision.

So I think we expanded sometimes at the start before we could handle that capacity. Basically. That was one of some of the challenges.

So, you know, especially we started in the Triangle area, so local we could, we could at least get to the fields ourselves. We could manage stuff like that. Kind of like Uber took San Francisco first, but we quickly went to Florida because there was a big need down there.

Probably, probably about eight to nine months before we were ready to, to go down there. Even from the product side, Joe was before we had like the geolocation fully set up, everything like that.

We were very much the kind of hustling startup of, hey, you know, we'll figure it out on the fly.

And we did figure it out, but I think for our, for our health and stuff like that, it probably would have made more sense to be a little more strategic and understanding that we don't have to say yes to every opportunity that came in, in the door. And so that's, that was definitely one of the challenges and then just the usual kind of growth challenges as well on the, on the fundraising side.

So it's, it's interesting. I had, I had no background in that before we started and jobs I was as a founder, I was involved in all of that.

And some of the challenges there are just like, you know, you believe in it, you're seeing traction, you want to go there. But, you know, the VCs have the carrot. You know, hey, once you hit this, you know, we'll chat to you. Once you hit this, we'll chat to you.

So that was one of the other kind of challenges is, you know, it's a, it was a less Sexy market is the best way to put it. Youth sports officials, then you know, it's not like AI right now, you know, or at the time, the blockchain was big.

So if you just put blockchain in front of everything, Rome was super excited. Whereas with us, we were trying to. We were very much.

They knew it was going to be kind of like a land fight, you know, a knife fight into each area, low growth and stuff like that. But once you had the flywheel, it was magic.

But they were happy to kind of step back and wait for us to solve that problem and then come in versus versus initially being like, oh cool, this is an idea. You see some folks get funded with like really cool ideas and they have then the capital to work.

We were very much kind of nitty gritty, roll our sleeves up, generate the revenue, was helping generate like business. And then we started getting the funding and that definitely helped.

Did you three co founders all get along just fine the whole way through?

Like, we're still all friends now and like we still actually was chatting to them yesterday, so we're still all there. But I definitely think during times we probably each. And it was never like one versus one versus one.

I think at all times it was almost like a rotating cast where I'm guessing one of us wanted to murder the other and vice versa for different reasons. So there was definitely some. I always joke as well. When we were starting out, we kind of said like, hey, this is like a marriage.

Not that any of us were married at the time. We were like, this is like a marriage. There's going to be days we want to like kill each other. And that was. Some of our advisors were awesome.

They said that they were like, hey, some days you're not even want to be in the same room as the person, but you have to remember why you're starting out, what the mission is and that you know, you know, life will go on post company. So just always bear that in mind. So my advice to any founders there are, make sure you can be around your founders even when you.

Even when you wait when I kill and stuff like that. And always try and fight.

Always be like proactive with the communication if stuff is frustrating, you know, as long as everyone's pulling their own weight, you know, that's. That's the most important thing in my mind. I was lucky there where my founders, you know, everyone had a different skill set.

So we all pitched in and I always like, look at it as almost like a band, you know, no one wanted to be A solo artist. And each brought a specific flavor to the team that like, you know, one of my, one of the founders, Daniel, amazing at sales.

I wouldn't have been able to get these contracts ahead of time when we were very much like, you know, ideation, hey, do we, do we know how this is going to work? He was able to sell it amazingly. And then Brendan, who is our CEO, was amazing at being able to like, cultivate those investor relationships.

He had the marketing background as well, so he helped us on that. On that side and stuff. So we each had a kind of a different flavor. And then, you know, sometimes we probably thought that one person should.

We should be spending more time over here versus here. And that's where sometimes we're at loggerheads of each other. But eventually we all came around.

And it was funny, as the company grew and there was more of us, those challenges were actually went away because we remember we were in like, as we cop.

Think, for want of a better word, we were all in the foxhole at the beginning together, you know, when there was just an idea and a piece of paper, no lines of code, all that sort of stuff. So when, when there was challenges, we always had each other's backs and stuff like that. So I was pretty lucky there.

And did you guys. Are you familiar with the concept of a. Of a tax form called an B, which is what founders. You are.

Yeah, yeah. So I was not aware of that initially and I think. I can't remember. I was at 30 or 90 days, you get.

But whatever it was was we had 48 hours to file it before, before we missed, we missed the window, basically. We were kind of going about our business and so I forget was one of the, one of the folks in like a co working space and rally mentioned something.

He's like, still kind of crazy. You gotta mail in your 83B. And we were like, yeah, yeah. We're like, what's that? And we googled it and we're like, damn. And then we, we.

We got it in on time.

Good. That's good. It's. It's. It's weird that, that such a critical thing for founders to, to. To. To do. To know about is still quite obscure.

Yeah, it's, it's what? It's wild when you think of it.

Like, you're like, yeah, when I think of it, because we were, we were in a mad dash to get to the post office, get it registered, all of that stuff. And you're like, how is this not like step one of you read like, hey, this is what you need to do.

Or when you're starting out, basically you're getting your LLC formed and all that stuff.

Yeah, but see, once you've done it once and you, like, almost, you know, don't get it done in time and you know about it. And you do it on day one. Exactly. On day one.

Yeah, that's exactly. Yeah. So it's one of those ones you don't know until you don't know. And that's what was funny.

I had watched the show Silicon Valley before I started Silbo and Joe. Still amazing to watch, even if you don't know all the little nuances.

But then when you're watching it and you hear like little nuggets like that or the 4A, stuff like that, and you're like, oh, yeah, yeah.

So it's super interesting as you go back through the journey, like certain stuff that you take for granted or you just glaze over and then you're like, these are actually critically important for the housekeeping of the company.

Well, final question about Silbo would be, so did that sale to NBC do well for you guys?

Yeah, our investors were happy is the best way I put it. But it didn't mean I got to go travel the world and go live in Bora Bora. But it was. It was really cool experience where we consulted for a while.

The idea was they were taking our technology platform, adding it on to Sports Engine, and then rejigging it a little bit to add in some volunteer work.

Because Cooley, you know, the kind of best way, like when you think of like legacy Twitter and the hashtags, is our users started using the product in ways we hadn't anticipated. So we were. We were basically nuts and bolts for sports officials, and we handle the payments and all that jazz.

But what they started using it for is event staff and volunteers and stuff like that, where, you know, ticket takers and everything that we were like, oh, well, we hadn't thought about that. So our platform kind of expanded. And that's what NBC saw is that's what they wanted to use it for, Sports Engine, basically.

So with the sale to go and through the due diligence, that was a really cool learning experience too. So working with their team, you know, and adding different stuff into, like our. Into our pipelines and like going through some code reviews and some.

Some different technology deep dives and stuff like that, it was really, really cool experience and made some really good friends through that too. So the folks that were acquiring it Guy Brandon Who I am still friends with and I chat to. He's gone on to a few different other companies.

We still kind of, we still kind of spitball ideas and stuff like that. So overall very positive experience.

So you did sport tech. Sports tech I guess would, would be what that's called, right?

Yeah.

And you've done fill in the blank tech in two other areas since then?

Yeah. So after Silbo I kind of was trying to figure out what I wanted to do next.

Like did we want to start another company, did I want to kind of go into a, into a larger company, go back or what I wanted to do.

Basically one of my investors had been invested in a company in Proptech at the time and it was very similar setup to Silvo two sided Marketplace where it was conn homeowners with trades professionals.

And basically what they were trying to do was take the analog home inspection service, ingest that data, extract it out, run it through their algorithms to produce a very simple one page digital estimate of hey, here's the stuff that you need to get done to your house. So you know when you're buying a house or if you're selling a house, you've got these little punch list items.

So it basically was automating that process.

And then if you were in one of the markets they worked in kind of similar to Silvo, you could, you could basically one click, hey, I want to get that work done.

So instead of you having to chase down someone for your H Vac, your electrical, your plumbing, your roof punch list, manage all of that process itself. So it was kind of this really cool project manager manager for your home as well. So super easy to use, really cool experience. And with their.

The initial plan was to go down, meet the team, kind of help stabilize some of the tech, almost like a consultant. And then I really hit it off with the new CEO and the existing legacy team were here in Charleston and I still live here because of all of them.

So really hit it off.

We had an office downtown and there was like 23 of us I think when I joined and within like 18 months it got up to 100, 160 people gone from like single digits revenue to north of 70 million. It was like super hyper growth. So really cool experience.

And it's part of that it was how do we keep this Joe keeping the systems online, keeping, keeping the scaling with how fast the company was growing and then also building for the future because you know there was a big data play that could have been that was actively being worked on too was we were consuming all of this home inspection data is like, hey, there's a way we can actually take this, monetize it, leverage it in predictive analytics around what could be needed for your home depending on like your flood zone where you are geographically, et cetera. Like that. So really cool experience in there. It was a different experience too is from.

Because this, this, the company had been founded by folks here in Charleston, a tradesman and a real estate agent. And they had really cool unique insights into it too. But they also did a really cool thing of like they hired some top quality operators.

So when I got down it was kind of fun. Like I had, I knew nothing about prop tech at the time or a lot, a lot about home repairs and stuff.

And you had like really amazing subject matter experts in house who like ran their businesses like it was their own companies type of stuff. So it was a really cool experience. And think we're all still friends who worked at that company.

A lot of, a lot of folks have moved on and stuff like that. The company now, I think it's. I don't know how many people are there at the moment.

So in both cases you had somebody that knew the market that you were then building a product for. So you know someone, in my experience someone has to be that person or, or a couple people. You know, you don't.

You can still be a founder and not completely know the market.

If, if your piece of the puzzle is like for example, building the product, as long as you have somebody that's involved with the definition of the product and what's, you know, a minimum viable product who does know that that market then it can, it can all work out. But you know, I've been in a situation where none of us knew we had only people that knew the product.

And then this was a classic example of well, if we build it, they will come and they never do. Hi there. I hope you're enjoying the show.

In addition to the podcast, you might also be interested in the online program I have created for startup founders called who says you can't startup in it I've tried to capture everything I've learned in the course of founding and running nine startups over 37 years with no constraints like there were with my book Tech Startup Toolkit. The program has four courses, each one about 15 video lessons plus over 30 high value downloadable resources. Each course individually is only $375.

The QR code will take you where you can learn more. Now back to the podcast. That's good. Now there was a third one another.

So a whole different market then. So as we with with Punch List and it got rebranded to bosscat after.

When I was in there I kind of, I kind of had a hankering to go back to my roots from SAS, you know, with the AI, NLP, etc. Natural language processing.

And with everything that was happening in AI at the time, I was kind of looking at an opportunity where I was like, okay, I want to get my teeth around that and work and like get out of the two sided marketplace and actually work on a pure product.

And that's when I joined I went into edtech, which was not something I thought I was going to go into, but it was again another interesting experience where I didn't go to college in the US So it was definitely a learning, it still is a learning experience for me. So joined a company called Ocelot. And the idea there is it's a communication platform for higher education.

So if you go to a university's website you'll see the chatbot in the bottom right. So it's, that's for the students for information so that they can be best served.

And then behind the scenes there's a platform for the university staff basically to manage their text messaging, live chat and their actual chat, their virtual assistants as we call them.

And in there too being able to have like the predictive analytics to determine like the pulse of the campus, how everyone's getting on, what's the general sentiment, et cetera. Like that.

And some of the stuff we're working on too was like the predictive analytics on retention and how to identify students at risk and everything like that.

So in there was actually part of the remit was coming in and helping lead the team as they were going through upgrading the AI basically from what had previously been built to leveraging some of the newer LLMs, et cetera, the different models that were out there so that we could modernize it to kind of keep up and jump forward to where, where the industry was going. So really cool experience there. And funnily enough, at the end of the first year there we actually got, we did it, we, it was another kind of exit.

We basically merged with a company called Gravity and Ivy. So one of our competitors was called Ivy. Very similar kind of space to ourselves. And then Gravity is more on the alumni engagement fundraising site.

So what it was, was the end of last year we did a merger where all three companies came together.

And as part of that experience, really cool first time that I had gone through that was I was given the task of being CTO to integrate the three different companies. So that's been my world for the last year. Whole different, whole different space as well.

Then, then building your product, getting it out there, getting product market fit and stuff like that.

This is definitely more of the, the day to day kind of integrations, strategic planning for the future, identifying where there can be kind of overlap work, organizing the team, et cetera. Like that.

So cool experience and getting to learn more about the alumni side of the house as well at the moment and ed tech and the unique needs that are needed there, especially around, you know, different laws that can be passed and stuff like that and how we, how we manage to handle all of that.

Sounds like you've really got the startup bug.

Yeah, yeah, yeah, that's, that's, that's true. A lot of different experiences from like as I joke, lighting the fire yourself, going into someone else's fire and making the flame bigger.

And then the other one is bringing some fires together. The best way I put it, to.

Create a bigger one, to make a total conflagration.

Yeah, that's it.

And it's cool because I don't like, it's an interesting journey, but I don't think I could have gone into where I am now without the middle part with Boss Cat and stuff. That and vice versa. I don't.

If I had gone into punchless Boss Cast Pass Cat, like say straight from sas, I think I would have just droned basically because I hadn't, I hadn't gotten those reps at Silbo basically where you know, a lot of times it was we don't know how to do this cool, we'll just go figure it out. Or like I wasn't what I call like in operations or rev ops or anything that cool.

Got to read every book there is on it, figure it out because there's only eight of us and you know, I need to figure out how to launch a city basically.

So it's kind of really cool experience because it stretched the tech nerd in me to actually learn more about like finance, marketing, operations, like you know, the classic founder, wear many hats type of thing, which I think stands stands to me as I go into different companies now because I always joke I'm the janitor, like I'll just take on any of the, like the bad tasks or like the lower trash tasks so that you can empower folks to work on the cool stuff. But that comes from the silver days where it was like, all right, cool, we need this.

Myself and my fellow founders would be like, cool, we'll learn how to do that.

Whether it's like cold calling referees to see if they want to join the platform or anything in between, we were happy to take that on, which is the Startup Venus that I think is what I look for as well when I'm looking for folks to join my teams and stuff like that. It's kind of that Angela Duckworth grit, you know, hey, are you willing to just roll your sleeves up, get it done, basically.

Are there any preconceived notions you had in the very early days about startups that you don't believe anymore?

Actually, I think you touched on. Something that resonates with me is, hey, if I just build it, they'll come. Like, the best product wins.

Like, it's, if you just have the best product and cool, it's all set, it's just guaranteed. And I always think of it as like, you know, if a tree falls in a forest, if you could have the best product ever.

But realistically, without sales and marketing, no one's going to know about it, right? So I think I definitely underappreciated those at the start where I just thought, no, it's all about product and engineering.

Like, you know, this is X, faster than this. That's all that matters. And realistically, people don't care.

So you, if you have like an elite level of marketing and sales, you know that, and an average product, that's going to be an elite product and average sales and marketing from what I, what I other preconceived notions I think were, I think as well as around like risk profile. I, I, I know when I left sas, everyone said I was crazy because, like, there's an average tenure of like north of 20 years.

There's, I assumed as well it would be a lot easier to find folks who just wanted to dive in, build startups and stuff like that.

But actually that was a little harder in the, I think the triangle has grown a lot now, but that was a little harder to identify folks who are willing to kind of take that leap as well. Which is something I probably didn't appreciate in myself for like the risk profile I had, you know, versus some other folks.

So those are some of my preconceived notions. I just assumed everyone wanted to do it because I always wanted to do it.

One of the things we try to do here is give advice to startup founders. So what advice would you give a first time founder thinking back to your Silbo days about building a tech team?

So no, great question. I go back and forth in a few of it.

I default as well to a lot of reading and stuff like that, which I know is not as a sexy sounding or like the silver bullet that folks want to hear, but there's a few different things.

So like on the technology side building your team, it's a few things would be making sure that you have your structures in place, you know and like you know exactly how what you want from your teammates because everything's going to change, your product's going to change and everything like that.

But understand what type of profile it is that you want people to come in and also be honest with yourself of like where you have gaps, you know, not everyone can do everything basically like are you strong on front end, mid tier, do you need some DevOps help and stuff like that?

And that's kind of how I approach it first because like your first probably two to three hires should be generalists who can kind of dive in and do everything. But it's important that you have like ultimate trust with each other as well.

So that's a part of like the building it and making sure that like celebrate the small wins, right? You know, like shipping fast, getting something out there. A lot of times you can be like oh my God, we have 50 more things to do.

But you need to celebrate those small things because it's the journey is the most valuable thing I think of being as part of a startup like everyone wants that exit at the end, but it's actually the journey. You look back and like make sure that you appreciate it with your team and build that culture.

Because culture is hard to build and easy to lose and it sounds kind of like wishy washy but it's like having those small wins because everyone's going to be probably working a lot more than they would in an enterprise. That's just when I interviewed people I always said look, this isn't a 9 to 5, this is a 9 to getting it done basically role.

But it's that it's celebrate those wins, build that relationship. I've gone into three different companies now and my original team is, has come with me each time because we built that camaraderie together.

Like we, we know who has gaps where, how we work well together. And my other thing is like educate yourself Especially if you're the technical side. Educate yourself to get more well rounded.

Like the Secrets of Sandhill Road is a great book on like VC investing. I knew nothing on it and I recommend like getting knowledge on that because you're going to be pulled into fundraising meetings regardless.

And understanding like the atmosphere, how to, how to handle them, what they're looking for, why they're looking for it. You know, like a lot of times on the technology side it's like, oh, but I just write code and it works, whatever.

And you know, people have seen the social network and they think that's how it all goes, whatever. So I think like educating yourself, reading different books, understanding too, like, you know, what different skill sets bring to the team.

Because if you're coming from larger companies or if you're coming straight out of college, you might not, mightn't appreciate all the stuff that say a customer success manager has to do a CS person, things like that. So my thing is for technology leaders is also to make sure that the customer is in the room with you.

Like, not literally, but like making sure that you are not building in a box. Like have that voice of the customer. Even as you're building your team, make sure that your engineers know that, hey, the customer's voice matters.

Customer success. Meet with them regularly.

And a lot of times it could be yourself, you could be talking to yourself, but making sure you're actually bringing that information into the team as you build it so that the team can understand that cadence too. Of like, hey, it's important what we're doing, but it's also important that we're listening to what the customers like, what they don't like.

And that'll help frame your product direction too. It doesn't have to own your. It's not the tail that wags the dog, but it's important that they're in the room.

And as you build a team, that the engineering team understand that you're one team.

You know, sometimes I've come in places and I've seen fiefdoms, it's important to break down those, I think at the start because the best ideas come from everywhere, basically.

So making sure that the team you're building is open, transparent, trustworthy, that's kind of my advice to folks and just read as many books as you can or blogs and kind of pick, pick what works for you, like frameworks, like, you know, whether it's agile, shape ups or whatever. Make sure to make sure the framework that you want to set your team up in works for you.

And you're not just copying something because, you know, company A did it, but it doesn't work for your team.

Make sure that you're adaptable and that, you know, you come up with a framework that empowers you, makes you be able to, like, deliver the velocity that you need.

I think with that question, I. I think with that question, I got the Irishman talking really fast.

Yeah, yeah. Yes. You probably want to slow that one.

That's okay. That's okay. That was a. That was a fire hose, but that's okay.

That's okay. There was a lot of.

Hey, so, last topic is. So it's kind of cool that you mentioned Angela Duckworth.

She's kind of real important to me because I spent a lot of time thinking about and talking about and writing about grit, and. So what is your source of grit? Where. What is your grit story? Tell us that.

Oh, where. Where I think my grit comes from. Is that. Yeah, think. I don't know. Yeah, it's a.

It's kind of an interesting one because when we're trying to hire, we always try and think like we're trying to measure people's grit, you know, and it's kind of like almost immeasurable or whatever. For me, I don't know. I don't know how best to do it. It's just like, I always like being told I can't do something and that.

That motivates me or whatever. I don't know where that comes from and all that sort of stuff. So, like, being taught, like, you can't do this. You won't. You can't hit this deadline.

You can't do it. That. That's the kind of fuel to my fire. And that's been since I was a little kid, basically.

So the more I'm told I can't do something, the more I. I want to do it, basically.

So, yeah, you know why I'm laughing right now? Can you see this book over here?

The Tech Startup Toolkit?

Is it right next to it?

No. No, I can't see it. A deadly class.

So that is like my mantra. Who says I can't. In fact, up there, I can't get it.

I can't reach it for you, but it's the United States of America trademark in the phrase, who says I can't see?

I love that. And that's. I didn't realize that about myself. I suppose I just always assumed everyone was like that.

And then when we were doing Silver, one of my co founders, I heard him Say that one time he just said one word to use was like relentless. And in my head I was like, because we had a crazy deadline and like it didn't look like we were going to hit it. And I was like, what?

We can, why can't we? Like, why can't we? He's like, because it's not feasible. I was like, why not?

Like, and, and when you break it down, like was that saying, like there's, you either can or you can't, you're going to be right either way. So just, just keep going, keep doing it. So that's like, it's just, I don't know.

And it might be as well like I grew up playing like those Irish sports and then rugby and stuff like that where you're not necessarily on the ball all the time and stuff like that and you just gotta dig in and kind of do some of the dirty work, which I think and then the team wins. So I think that helps too. So maybe that's, that, maybe that was what helped shape me playing, playing some rugby.

I don't know. I think Irish just, that's right. There is a, is a big part of just. You could just say, where's my grit come from? I'm friggin Irish.

Yeah, true, that's true. We're all, we all survive. So we're just Irish and we're just like, we're just gonna get it done. Basically. That's the.

Well, I got, I'm going to tell you one, who, who says I can't story of mine, which was. So I started saying this because when I was 16, I lost my leg and people were telling me all the things I can't do and it was relentless.

It was, it was, it was actually shameful the way they did, did it. So I fought back, you know, all that. And then I had my sports that I got good at with one leg. Skiing and, and swimming were the main ones.

And then one day somebody at work was going to do a four day bike ride, fundraiser, bike ride from Boston to New York City and asked if I would contribute for the, for the fundraiser. And I said of course I will. It was a good cause. And I was just so impressed.

This young lady was, was, was, was athletic but you know, this was beyond what she'd ever done. And then later I was bragging about her to some of my team. I was the CEO, the senior team.

And one of them said, you sound so excited about this, it's too bad you can't do that. So I bought A bike. That afternoon I trained like a mother. And the next year I did it on one leg with a, without a knee.

You can't really wear a prosthetic. It's not safe even. It doesn't help you at all. So I, I did the ride from Boston to New York.

I was scared out of my mind when, you know, I trained hard. But when you go from here to, to New York, you go through some very steep hills. Well, you're on the back roads, of course.

Now the freeways, they smooth it out and so you hardly notice that. But there's some significant hills in Connecticut.

Genie and I get to the first one and all the two legged people are bunching up at the bottom of the hill and they're starting to walk their bikes up. That made me more nervous. It's like, my God. Because how do. There's no option for me to hop up the hill.

Yeah.

And if I don't make it up the hill at the midway point, what do I do? Then I got to go back down to get back on my bike if I come out of the pedal. So there was no option but to just bear down and gut it out.

And I started passing two leggers who are walking and then I, I couldn't figure out what was going on and what was happening behind my, behind me because I'd passed them, they were all getting back on their bikes. They said, well, if he could do it. And they, and they thanked me later for motivating them to work harder.

That's awesome.

And so that's, that's my. Who says I can't?

Yours wins by a country mile. That is, that is epic. I love that too. And that's inspiring. Fair play to you. That's, that's unbelievable.

I love that, that you went past and people were like. Because that's, sometimes people need to see that. Right?

They need to see someone who's like just relentless and hey, I'm going to do it no matter what. And then that drags everyone with them.

Well, that, and I've, I've used that, that whole, you know, gestalt in my startups, you know, because basically nothing in the startup can ever be as hard as what I've already been through and, and, and conquered. And that really helps. And, and that's why I think all startup founders have grit. Have to have grit. It's their fuel, it's their power. Right?

Yeah, I agree with you.

That's, that's, and I don't, I don't imagine you'll Ever go back to a big company?

No, that's the thing.

It's, and it's funny, a few of my friends who, from big companies who've left to go to startups, I was explaining to them like how like how addictive it is and I remember like two of them had left and they'd gone to a startups like series B, series A, Series B companies and instead they're like, oh my God, I should have done this like six years, five years, ten years earlier. Like, this is way better. When you're in the right one, there's just like an energy in the team and it's just exciting and stuff like that.

So that's, I remember like at my startup it was like you didn't want to close your laptop, right? You're just like, oh, cool, next problem, next problem. So that's the kind of energy that startups bring.

The right ones, when you're around the right people.

What I, what I've discovered is that even, even the bad ones, I don't mean it's a, it was a bad experience, but I mean it had a, it didn't have a good outcome, but the 9/10 of the time was a joyful experience. And it's, it's a certain amount of, it is a control over your own destiny. Another is the energy in the team.

And a lot of that comes from its, it's, it's a team built out of trust. You, you talk about the way you, you did it.

I, I've sort of instituted a policy when I started a new company, which is in the first 25 employees, I say to everybody, we'll hire no strangers, meaning we're not going to go recruit. We're going to use who we know because we've done this before.

We're going to pull them in, they're going to pull who they trust in and you trust them by, by association, you know. Well, someone I really trust, trust them and you quickly get to 25 without having had to go outside of your community.

Now that doesn't work on your first one.

No. I love that idea though. That's awesome. But yeah, I'm going to have to borrow that. That's a great one.

Well, you could borrow any of it because one of the. My thank you gift to you is going to be a copy of this book.

I'm looking forward to it.

Yeah, yeah. But thank you so much, Seriously, Paul.

No, thanks so much. This has been great fun and congratulations on all your success as well. I'm excited for that book.

I know I was going to buy it and you said to wait till we've done the chat because I'll have it. So I'm excited to read it and then pick your brain on some other stuff.

Great. Great. Well, we're, we're. We're now friends. Thanks again. This was a very good episode.

Legend. Thank you very much, sir. Have a good one.

Now your startup founder toolkit Number one Master the art of strategic no. Paul's biggest mistake was saying yes to every opportunity that came their way. Expanding to Florida before they were ready.

Learn to recognize the difference between good opportunities and right time opportunities. Sometimes the most profitable decision is turning down revenue that would stretch your team beyond capacity. Your first instinct should be to say no.

Then make them convince you why it should be yes. Number two, don't fall for the best product wins Myth. Paul initially believed that having the superior technical solution guaranteed success.

A costly assumption.

In reality, an elite marketing and sales team with an average product will consistently outperform an elite product with average go to market execution. Spend as much energy on your sales and marketing strategy as you do on your product development from day one.

And number three, build your team like a band, not an orchestra.

Paul's secret weapon has been building teams where everyone brings a distinct irreplaceable skill set, like band members rather than interchangeable orchestra players. His core team has followed him across multiple companies because they've developed unshakable trust and complementary expertise.

Hire for unique strengths that create interdependence, not just competence that creates replaceability. Now go find your band members, those people who complement your weaknesses and amplify your strengths.

Because like Paul discovered, the right team will follow you from startup to startup, turning every new venture into a reunion tour. That is our show with Paul. The show notes contain useful resources and links.

Please follow and rate us at podchaser.com/designing successful startups. Also please share and like us on your social media channels. This is Jothi Rosenberg saying TTFN Tata for now.