Podcast - Building and Scaling a Business Through Leadership, Adaptation and Delegation

Patrick Driscoll: Welcome everyone and thanks again for tuning in to "The Innovation Imperative." My name is Patrick Driscoll, and I'm the Director of Client Development for Emerging Companies and Venture Capital (VC) at Holland & Knight, where we work closely with founders, VC firms and investors navigating the full life cycle of innovation from company formation and early fundraising through growth, scaling and ultimately that exit. A big part of our role sits at the intersection of law, capital and storytelling, helping innovators and investors think strategically about how they build, fund and protect what they're creating. "The Innovation Imperative" is really about that journey. Each episode, we sit down with founders, investors and operators who are shaping the future, often behind the scenes, to unpack the real stories, lessons learned and inflection points that don't always show up in pitch decks or press releases.

Today's conversation is one that I'm pretty excited about. It's a practical, candid discussion on building and scaling founder-led businesses, navigating inflection points and leading through change. Joining me first is Cliff DeGroot, my colleague at Holland & Knight. Cliff is a partner based in Portland where he advises startups and investors and a variety of other clients on things like company formation, financings, governance, M&A matters, and Cliff will be leading today's discussion. But more importantly, we have our special guest, Allie Persitz, who is a serial entrepreneur, operator and investor with a track record of building and scaling high-growth companies. She's the former founder and CEO of Hubb, an event technology platform she built based on first-hand industry experience and successfully scaled and exited. Earlier in her career, she led Dynamic Events, growing it into a nationally recognized experiential marketing company. And today, Allie is deeply involved as a founder mentor, investor and operating partner, working closely with companies on go-to-market strategy, leadership and navigating moments of transition. So with that, Cliff, I'll hand it off to you, and let's go ahead and get started.

Cliff DeGroot: Thanks, Patrick. Allie, thank you for talking with me. I am curious, I know we've talked about it, about your past and how you initially got into the events business.

Allie Persitz: You know, being a founder, a lot of times when I am talking to people, it's the ones that have passion for what it is they're doing, and for me, that started when I was 18. People tend to laugh a little bit because they sort of see the end result of my career, but at the very beginning of my career, I was a street racer. And I loved getting groups of people together and the energy that came from it. And so I actually started my first company when I was 18, using $1,000 that I had saved from Old Navy. And I rented the local fairgrounds and threw a car show just to bring people together for an experience. And that one was successful, and one grew to two to four to six to 10, over six years I built and scaled my first company in experiential events.

Cliff DeGroot: So how did your early experience as an organizer of street races and other companies shape the way you think about leadership and execution?

Allie Persitz: You know, it's funny, my parents always told me, you know, I'd come home from street racing in the middle of the night and they'd be like, "What are you doing with your life?" And so now I remind them [of] that and I try to remind myself with my own kids that, you know, our experiences, both good and bad, really just form who we are. And for me, leadership development and growing and scaling teams is all about understanding people. What makes them tick? What makes them feel like they want to contribute and that they're seen in their contribution? How do you get them to work together with other people to achieve greater things than we could as individuals? And how do we have fun while we do it? I think as we get older in our careers, we also want to have fun. We want to be a part of a team that we enjoy being on and that can produce really great results. And so for me, even at 18, throwing these experiential events, I think what I very quickly realized is that the journey and how you get people excited about the journey and the vision really allows them to lean in and produce great results.

Cliff DeGroot: I love that. When you started Dynamic Events and later Hubb, what problems were you solving for?

Allie Persitz: Yeah, you know, from a services standpoint, there's a couple things that I'll say. One is, my car show business failed. And I had scaled from one to 10 shows, went across the country, and then realized that union labor meant all these extra expenses that I wasn't aware of and the market dynamics were changing. I ended up $100,000 in debt because I was using my credit card to pay my line of credit, my line of credit to my credit card, I got real good at that. And at 24, I thought my life was completely over because my first company had failed and I didn't know how I was going to pay off this $100,000 in debt. And I think it's really important to talk about our failures as well as our successes because that moment has stuck with me my entire career, of failing and having to restart over again. And for me, part of that was figuring out how do I take the skill sets that I have and the experience that I have and practically apply it into something that's needed in the world.

And so for me that meant taking event experience and applying it into corporate events. And that's actually when I started working at Dynamic Events. And I started in an entry-level position there. Microsoft had a need of, you know, promoting their products and services and getting closer with their customers and partners, and our team was really great at planning those experiences and managing them so that they had a really big impact on the business. And for me, you know, I talk about entrepreneurial mindset a lot to people, I talk at a lot of colleges because you don't have to only be an entrepreneur to have an entrepreneurial mindset. An entrepreneurial mindset can apply to just how you think about the world. So your question of like, how do you think about the problems that you're solving? That's entrepreneurial mindset. It's literally like, how can I do something better than what is being done right now? And so as a part of events, it was, how do we change this up so that people are experiencing things that they haven't experienced before? Or how do we put them in scenarios where we're changing their hearts and minds and their sentiment about something because of the experience and the engagement that they're having?

And so early on in my career, I think a lot of my mindset was all about how do we do something better? And so at that time, fax machines were technology – so that's when I always age myself to say fax machines were our tech, but they were – and I was doing these big events for Microsoft and I was tired of getting burnt out. We had spreadsheets and emails and, I mean, we would just be trading so much information back and forth because the events that we were managing were massive. You know, we could have 1,000 speakers for any given event and then they would, you know, send us an email and say change the period here, add an exclamation mark here. And you wanted to just go nuts because not only did you have to change it in a spreadsheet, you might have to go to an FTP site – also aging myself there – but we looked at this and said, this is so inefficient and we're spending so much time on this, how do we make it better? And so that's really a question throughout my entire career that I've just continued to come back to, which is, how can we do this better? And if there's an opportunity to do something better or different, then it's well worth the risk of being able to look at changing it. And that's actually how Hubb was born. It was me wanting to get out of spreadsheets and email, managing large volumes of data and deciding to go build software because I knew that software would be a better way of doing that thing.

Cliff DeGroot: So how'd you actually know that Dynamic Events was a real, scalable business? At what point was it that you're like, yes, I can do this.

Allie Persitz: Well, so when I joined Dynamic Events, there were about 17 people in the company, so smaller company. The other thing that I talk about is the fact that I have been a company of one and I've also ran a company that had 2,500 employees across 17 countries. So there's a very diverse background and skill set that I have been able to participate in, and scalability applies at every single level. Scalability of one is, you know, maybe 22 hours a day, you might need a few hours of sleep, at least for a short amount of time. But scalability to me is about creating opportunity. So if you're able to look and say, OK, I'm going to do this thing or produce this product, people want it, well, then you just continue to build off of product-market fit. It's like, OK, what I'm doing matters, people want it, I am going to continue to grow. And part of that is also never saying no. I mean, in growing all of my businesses, a lot of times I would say yes when I didn't have a clue how I was going to actually make it happen. And so for me thinking about scalability back at the time of Dynamic Events, I ended up buying the company, firing everyone, and it was literally just myself. I had to convince Microsoft, at the age of 24, that I was allowed to run all their marketing campaigns with one person. And then I very quickly had to figure out how to scale a team.

I work with a lot of early-stage entrepreneurs, because that's where my passion really is, and when we're scaling, it's really about finding people that are aligned to your why and to your vision and your mission and continuing to make sure that the quality of what you're putting out there maintains the bar to continue to scale. And so at Dynamic Events, it was just continuing to hire people, continuing to run more events, saying yes to every opportunity that came, and then it was the same thing. I didn't know how to build software, but I saw the opportunity and I said yes, and I used it internally at Dynamic Events and then realized I'd built something of value. And so that's when I decided to go raise money for it, to be able to scale. And a lot of times people say, well, how do you know when the right time is to be able to scale? Well, to me, the right time to be able to scale is when you can't handle the volume that's coming in. You don't want to scale ahead of time and just hope that it's going to show up, you actually want to get to that product-market fit and feel that momentum, and at that point, that's when you really put fuel onto the fire. And in today's financial climate, you know, back in 2015, 2017, when I was raising money, it was all about raise as much money as you can and spend it as fast as you can to try to just grow as fast you can.

And in today's climate, one of the things I was really grateful for as we went through COVID is the fact that I had been a bootstrapped entrepreneur and I knew what financial responsibility looked like. I know how to run a profitable business and how to think about scale at the right moment so that you're spending money in a way that's actually meaningful. So scale really is one of those things where you want to make sure that you have the ability to be able to have the revenue runway to be able to invest in the way that you want to invest.

Cliff DeGroot: It can be extremely challenging building out a team, and you obviously have an incredible experience building teams internationally, but how do you go from a team of one, yourself, to, I can't even recall how many employees you had when you ended up selling it. How do you determine who the right people are?

Allie Persitz: Yeah, you know, so when we sold, we were about 150 people. And that's very different from one, you know, and I think companies go through these growth spurts, and, you know, zero to five is a different experience than your five to 20, than your 20 to 50 and then your 50 to 70. And so I learned these things the hard way, right? It's like, every time you hire X amount of people, you go, oh, shoot, I wouldn't do that again. And so you sort of build this arsenal of things that you know you wouldn't do and that you would do. And when I was first growing Dynamic Events, a lot of it was hiring friends and family. And I didn't really reflect on this until later, but I knew it was because their values aligned to how we did what we did. And ultimately what I found in building companies, regardless of whether it was 10 people, or it was 150 people or 2,500 people, it was about getting people on the team that believed in the "how" and the "why." Because the "what" can be taught. And so that's why when you're building a business and people ask you about your vision and your mission and your values, some people roll their eyes and they're like, oh, that's boring. It doesn't have to be boring. It can actually be the letter of the law in terms of how you build and scale your business and the type of people that you bring in. Because if you can hold them accountable to the values in which the company upholds, hiring and firing and making sure that people are on the right track becomes a lot easier because you're all marching to the same order versus something generic or just, you know, it's all about the what.

So for me, that was a big part of being able to hire appropriately. It was being really clear in what we're looking for. And so when we had interviews, we would actually ask people, tell us which core value you align to most and how does that show up in the day-to-day. Or we would give them scenarios saying, OK, here's a customer engagement, we'd sort of put a twist in there of like something going against the core values and ask them how they would manage against it. Because ultimately at Hubb, we ended up having a really great people champion – that's what we called our HR, people champion – and a lot of her commentary was, we're all adults. It's not like we walk in the front door of the business or turn on our Zoom now and drop all responsibility and have to be told what to do. Like at home, we have to manage our bills, our family, our responsibilities, everything else. We're grown adults, so why do people assume that in a company they have to be told what to do, and then you're penalized if you don't? It's more like these are the rules, these are boundaries that we play within. As long as you're playing within these boundaries, you're responsible for the results. We didn't have PTO, we had unlimited PTO. People could take as much time as they wanted off, but you were damn sure that you were going to get your job done. So I didn't care if you took Friday off if you already got everything done that you needed to do for the week. I wasn't going to micromanage that. But if you weren't actually doing what you said you were going to do, and you didn't do it in a way that aligned to the company culture and values, you're out, because the rest of the team is high-performing and is able to work together in those capacities.

Cliff DeGroot: In terms of your growth, what were the major challenges that you faced other than just finding the right people? It seems like you handled the whole scaling of the business and the team and the culture really well. But I'm assuming there were bumps in there that you were like, do I just toss in the towel? What were those pieces?

Allie Persitz: You know, I think anyone in business can sit and tell you horror story after horror story after horror story. You end up learning a lot through your experience. But growth is hard because a company of one or a company of 10, a company of 50, is very different because it no longer can be all about you. Like I mentioned, working 22 hours a day, if you're a company of one, well, you have complete control over what you're doing and how you're doing it. And even when the company's small, you still sort of micromanage and, you know, you can be a lot more controlled in a small environment. And as you get larger and larger, it becomes harder and harder because you can't be everywhere all at one time. And so I think growth in a company sometimes is limited by its leader because the leader has to learn how to actually delegate things and to be clear in what the expectations are.

So one of the things that I always encourage entrepreneurs that I'm coaching to do is, if they're going to hire someone, have that person write what a job well done looks like in six months, have them write it, and then have them tell you exactly how they're going to get there. So here's a six-month plan, a three-month plan, a one-month plan, a two-week plan, a one-week plan. And if they write it and you agree, yes, that's what success looks like, yes, those are the right things to be focusing on, then they're off and running. A lot of people say, oh, I didn't train them enough or I couldn't meet with them enough and they put it back on themselves, and you can't scale one. You have to figure out how to get everything that's in your head out, and in a way that people know what success looks like and that they're able to march towards by themselves. And a lot of leaders end up getting caught in those growth cycles because then what you have to do is you have to train your leadership team to be able to do the same thing. So then you go from just being a team of one to now maybe you have five in your executive leadership team, but now you need to elevate all of those leaders to the point of being able to delegate and hold people accountable, not by doing the work, so that's the important component of this is that it doesn't mean you do the work.

And so often there's this definition that I work with executive teams on, which is, are you working in the business or on the business? So whenever they are working on something, it's a question of, is this on the business or in the business? Because if it's in the business, that is not high-value time. If it's on the business, that is high-value time. So if you start to look at your tasks and orient how much time are you spending and tactically doing things versus actually moving the business forward and coaching and managing other people, it can be really eye-opening in terms of your own leadership style and how you're managing your team for scale.

Cliff DeGroot: You kind of touch on a subject there of growing the team and having the individual team members picking things up. For you, what were some of the hardest things to let go of as the company grew?

Allie Persitz: I mean, I am a type A control freak, so everything. You know, the hardest thing for me, and I see this time and time again, the hardest things for people to let go of is typically the things that they enjoy doing the most. And sometimes the things that you enjoy doing most aren't the things that are the highest value for the company. And so, you know, as I continued to grow, it was like, I wanted to be the one managing the largest-scale events and, you know, working with these top executives. I didn't need to be, but it felt really rewarding to be able to check the box and be able to be good at something very tactical versus strategic, and oftentimes we don't see the result of that for a really long time. And so oftentimes founders will have some type of specialty – some people it's products, some people it's engineering – and we're always drawn back into that thing because it's why we're there. It's our passion. It's why started it. It's what we're good at. But I think over time you have to learn to be able to hand those things off and empower the other people around you and to not get angry when they don't do it the way you do it. And that is also another really tough thing for leaders, is to be able to say, I defined a job well done, it meets the criteria, it's not how I would have done it, but I'm happy with it. Even though you're, you know, it's painful for you to say that because it's not the way that you would do it.

Cliff DeGroot: Looking back and learning from mistakes, what's one scaling mistake you've learned from the most?

Allie Persitz: I think to not move too fast without data. So when we raised our second round of funding, I think there was a lot of pressure to just go out and spray and pray, in terms of marketing. And we ended up growing really fast because we could, not because we actually had data and a specific plan on how it was going to be successful. So, you know, from a scale perspective, there are times when you have to accelerate really fast, but you have do it in a way that has data for you to know whether you're being successful or whether you are not, so that you can be really quick and agile to be able to pull the plug or continue to invest based on the data that you see.

And a lot of times, people talk about smart goals, right, they need to be measurable and actionable and all these different things. And then people put them together and it's not an actual data point. It's like this nebulous thing that people are like, yes or no, maybe. There should be no maybe. There should always be, this is the exact number that I'm going to do or this is the exact impact that I am looking for, and then using those things to know whether scale is working or not. Because death of an entrepreneur ends up happening when we run out of capital and can't raise the next round and then we've spent all the money and now we're stuck. And so really being smart about scale is really important as you manage your cash flow.

Cliff DeGroot: In moving past scaling into pivots, I was wondering if you could talk a little bit about shifting from services to software and how that change impacted how you ran the business.

Allie Persitz: Well, I can tell you that my first engineering team hated me because I'm used to being in events and everything has to be perfect in events. And in software, not everything is perfect. So, every time I would be up at midnight working on something and I'd find a bug, I'd be like, "P1, this is an emergency, this has to fixed!" And they're like, "Allie, we really need to talk to you about what constitutes an emergency, this is not an emergency." So, there was this level of detail and exactness as I moved from services into software that I had to learn to mitigate. But pivoting and being adaptable is one of the top skill sets that we have to have. And I mean, even if we just look at the last 10 years of time, we look at how business has so dramatically shifted and changed. And so pivoting and agility just means that you need to constantly be aware of the potential of what if. I always ask people like, who's going to come eat our lunch and what could that look like? No one could have ever predicted the pandemic. They asked me about, was my business recession-proof? They never asked if it was pandemic-proof. And five years ago, seven years ago, no one was really talking about AI and how, well, can AI just code all of this and it won't matter anymore? That wasn't a thing either. And these are really compressed, short time frames, right, so agility and the ability to be able to constantly pivot but not pivot too soon, right? There's this constant duality of like, we need to be aware, but we also need to continue the course.

And this is where data comes back into play. It's all about data. Like, what are the data points that you need to be measuring to ensure that you're looking at both short-term and long-term success? So for me, pivoting from events into software, really, and this is one thing that I really enjoy working with entrepreneurs that have a deep understanding of the industry, it becomes very easy to be able to pivot within an industry or even outside of an industry if we know how to ask really good questions and that we look for patterns. And those are two things that have really helped me in my career. So when I pivoted from events to software, it really was just about understanding what was needed. I had a background in events, I knew what was needed. I would ask all the clients, here's what's happening, what is it that you need to solve this? A lot of times we get scared about answering questions that we may not like the answers to, and those are exactly the questions that we need to be asking. And the same thing happened during COVID. Overnight, I lost both my businesses, both the events management – we were managing super high-scale events – and then Hubb was in-person event software. And literally overnight, both disappeared from underneath of us. So agility and pivot, pivot was like the bad word of 2020 because everyone had to pivot, but being able to ask the question of, instead of just sitting here and hoping that this is going to change back to normal, can I ask the questions of what's possible? And then can I pivot towards that and actually create a pathway to what's actually needed in our industry right now?

Cliff DeGroot: Two more questions for you, Allie. First one: I know you've been super active and it's been amazing watching you supporting and mentoring female entrepreneurs. I was just wondering if you could talk a little bit about why you're supporting that group so much and why you've taken such an interest.

Allie Persitz: Yeah. You know, part of it is, for me, female entrepreneurs, you can look at the statistics in terms of the amount of venture funding that they get every year, and it's been stuck between 1 percent to 2 percent, depending on how you look at the numbers, for the last 10, 15 years. And it hasn't really increased. And so as a female founder, one of the things that I found was, a), being a founder is lonely, regardless of your gender. But being a female and trying to raise venture, it's really hard when only 1 percent to 2 percent of the capital is actually going to scale your businesses. And so I have a real passion for helping women to understand how to show up at the table in a way as an equal, whether that's how we speak, how we change the conversation to make sure that there's equality in the questions or whether that's using data to make comparisons.

And women are different than men oftentimes in how we run companies and how we think about things, but different doesn't have to mean bad. And there's a lot of unconscious bias, it's not even necessarily conscious. It's like we sit across from the table and you're different than I am in a lot different capacities, and so how do we actually create a bridge to that gap? And so women, for me, there's this special place in my heart for helping them to create community, to help enable them with the information that helps them to feel like they can show up in a way that feels powerful to them and they're able to achieve those goals. Because ultimately, the only way that we change systemic issues is by talking about it and showing up in it. And so that's a personal passion for me.

Cliff DeGroot: Love that, thank you for doing what you do there. It is noticed, Allie, very much so. Last question for you. Coming back to legal counsel, how did the role of your attorneys and other service providers evolve as your company matured?

Allie Persitz: Oh my gosh, if I had one thing to say, it is get your attorney so early on before you even start your company. There is a reason why attorneys and accountants and these people exist, because your long-term success depends on your partnership with the team that you build. And that's not just the team that is internal and full-time employees, it's also the consultants and your lawyers and your accountants. And I will say, you know, sometimes as an early-stage company, it's really hard to think about investing the dollars that some of those consultants take, but it is well worth every single penny. There is a lot of infrastructure components, employment law, just things that you wouldn't think of that can put you in these giant pickles. And if you are proactive in the very beginning at working with your legal team and your accounting team, it just provides such a steady, even basis. And I was just talking to an entrepreneur right before this, which, the whole conversation was, how do you protect your energy? Because we have so much to tackle every single day and the list of things to do in a business never ends. The way you protect your energy is by working with the right partners and having the right infrastructure in place through your lawyers and accountants so that you don't have to worry about those basic things and you have someone in your corner when you need them the most.

Cliff DeGroot: Patrick, back to you. Thank you, Allie.

Patrick Driscoll: Fantastic. Thanks so much. This has been such an interesting conversation, I think quite impactful, and several takeaways as per usual. I was taking copious notes, hopefully these are useful. The first is, I love that you said, "Say yes first." Entrepreneurs typically will be able to figure it out later. So momentum matters. If you're wired like a founder, like Allie, hesitation often costs more than imperfect execution. So just say yes, and then you're going to build those muscles to figure it out and support it. The second one is scale only after a product-market fit. So when you're ready to scale, don't take too much money and grow at all costs. If you're considering a raise or a rapid hiring, is the volume real? Is it repeatable? Is it painful to manage without scale? If not, then perhaps you might want to wait a little bit. The third: Build teams on values alignment, not necessarily only credentials. So find folks specifically at the early stage that are aligned with what you think the mission of the company is going to be. I like that you mentioned this: Hiring and firing becomes clearer and faster whenever you are able to focus in on those value-aligned individuals.

Number four, growth requires founders to let go, even of the work that they love. So I totally relate to this, and I've heard founders who have built something based on a passion they had or a problem that they're looking to solve and they have to hand off the technical components of what they've built to employees as they scale, and it's tough, it's difficult. And then getting used to how folks are creating new solutions or solving the problems that you used to solve without your direct insight is a little bit frustrating for some founders. And then finally, data should lead growth in pivots, but don't wait forever. So there shouldn't be a maybe, like that quote that you mentioned. Use data to validate direction, model outcomes long-term, and move decisively once the proof points are there. And then, of course, my favorite one is Holland & Knight. Founders should have service providers locked in early. It really makes the wheels turn a lot more smoothly. Have good attorneys, have good accountants, have good tax and audit folks, good consultants, whatever it might be, make sure that you build a relationship with them early on.

With that, I'd like to say a thousand thank yous to Allie for taking some time out of her busy schedule to chat with us and, of course, to my colleague Cliff for leading an amazing conversation. We will catch you next time on "The Innovation Imperative" and tune in soon.