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Tampa Bay Tech Leaders: Joy Randels, Tampa’s Startup Junkie and Cybersecurity Evangelist

Joy Randels - Full Stack Talent Tampa Bay Tech Leaders

Joy Randels, coined The Startup Whisperer by Robert Trigaux in a recent Tampa Bay Times article, is one of Tampa’s biggest supporters. She has almost 90 companies under her belt.

Joy met with us in our Ybor office and talked with us about everything – startups, technology in Tampa, women in tech, and more. Michael joined us for this very special interview.

The enigma that is Joy Randels

Roxanne Williams: Looking at your bio, you’re sort of an enigma. Between startups, acquisitions, speaking engagements, cybersecurity, advisory boards – and the list goes on – it seems you’re involved in a little bit of everything. Can you, in your own words, tell us how you would describe yourself?

Joy Randels: A startup junkie. I think that’s the best way to look at it. It’s almost an addiction.

Roxanne: On your LinkedIn, I think you’re up to 89 companies? Is that accurate?

Joy: Either from a funding perspective or an advisory role or whatever it may be, yeah, that’s actually correct.

Matt Vaughn: What does that mean as far as type of involvement? I’m sure that it varies from company to company.

Joy: I have built 15 of my own. I have 3 now, and there’s actually another one coming, but it’s part of my holdings company.

New Market Partners is my holdings company and is what I make investments out of. There’s also Applied G2, which is a cybersecurity company, and Invision Communications, which is a physical security company that happened after the cybersecurity company, based on some customer requests. We do things like access control for facilities, connectivity and cabling, RFID stuff, magnetic locks like gates for big condos and office buildings.

A friend of mine has a saying: “When I invest in things outside of my scope, I become road pizza.” I think that’s a super good analogy. I get people asking me if I’d invest in their companies all the time, and I tell them I’m not the right person for them. If I know someone who I can refer them to, I’m happy to do that. However, I will not invest in any company that is not a pure B2B enterprise technology company. I understand where the niche is. And it doesn’t mean they’re not great companies, it just means I’m not the right person to be part of it.

As for the other companies: I have 2 IPOs, I’ve been acquired 9 times, I’ve had a couple of pretty pathetic miserable failures, and I’ve raised $357 million.

Matt: The money you’ve raised, that was for your personal companies then? Not the ones you have an advisory role with?

Joy: Yes.

Matt: Wow. That’s incredible. Well speaking of advisory boards, you’re actually on the board for a former interviewee of ours – Michael O’Rourke. What’s the extent of your involvement with Pocket?

Joy: I helped Michael with raising money and refining his business model. Also, I introduced him to investors, and I advised him on not accepting pretty bad deals.

On the startup movement

Roxanne: In the entrepreneurial vein, you seem to have a true passion for the Startup movement in Tampa. What got you involved with Startup Week and all the other startup events?

Joy: I was a judge at the very first Startup Weekend held in Tampa, done by Susie Steiner. She’s a very good friend, and she asked me to be a judge for that event.

I’ve been around for a while, and I built companies before moving to Florida. I’ve actually built companies in New York, Silicon Valley, Austin, Europe, and in other locations. To me, scaling is the fun part. A lot of people think it’s the idea stage, and the idea stage is ok, but honestly, there are a billion great ideas. Sitting here right now, we could probably talk for 30 minutes and come up with 20 ideas that would make great companies. It’s really about the execution on the other side. Scaling is the harder part, and to me, that’s the most interesting part.

At Startup Weekend, judges don’t usually go to pitch night. But I kind of broke the rules (which I do a lot) and I said, “I don’t want to participate, I just want to come hear the pitches and I’ll leave before the voting is done so I won’t know who’s ideas get worked on, and I won’t show back up until Sunday night.” So I listened to 40 or so pitches, and there was this one guy from Miami who had this really great idea. He got up and showed some wireframes, and I thought to myself, this guy’s really got his idea down.

I came back on Sunday and all the people came to pitch to us, and he wasn’t there. When I asked where he was, I was told he was not selected to proceed further. I flat-out asked why, since he had the best idea out of all of them. That company had the potential to be a billion dollar company. I went and I found him before I left, and I helped him meet a developer in Miami. He’s now out in San Francisco building his product. I was just so disappointed that they didn’t pick his idea and instead picked ideas that didn’t really work out.

At the end of the day, it’s a learning experience.

I think Startup Weekends are great. They’re good learning mechanisms. However, we’ve kind of turned them into a pattern here where the same people show up over and over again. It’s more of a social event than what they were originally designed to be.

Michael Sunderland: So how do we break that? I’ve observed that as well. It seems like the entrepreneur community is The Entrepreneur Community, in respect to where it’s the same people at every event.

Joy: But not the people who are building the real companies!

Michael: I agree! But how do you engage those people?

Joy Randels - Full Stack Talent Tampa Bay Tech Leaders - Building Real Companies

Joy: It’s a different kind of thing. A few Startup Weekends ago, a friend of mine who is on startup #4 texted me, “Why aren’t you here?” I’m busy. “Is this really it?” And I told him that yeah, it’s turned into more of a social event than what it was initially designed to do.

The goal of Startup Weekend – you can read this on Brad Feld’s blog – is to give you the fundamentals you need to understand how to vet an idea. “How do I do product market fit?” – all those core principles. Once you’ve memorized it, going back again and again vs. doing real work doesn’t build real companies. I think there are some people who have come out of that and built real companies, like Mark Lombardi-Nelson. Matt Spaulding has been a serial winner of Startup Week, and he has a development company. He’s a brilliant developer – and I do mean brilliant. He’s super smart, he’s a quick thinker, and I would love to see him take any of the ideas he’s come up with and start a real company. Because I think he could. The guy can write some cool shit!

If people want to build real companies, they have to get out of the mindset of “it’s fun.” Not that building a company isn’t fun, but it’s still a lot of hard work. You do it because it’s something you really care about and you want to find like-minded people to be your partners and be your first, core employees – because they’re the people who are going to get you where you need to go. You need people who have a similar work ethic than you.

I think that we like a lot of the glamour of it. However, what you’ll find is that the people building real companies here – guys like Mark Lombardi-Nelson – actually, Mark is such a good example. He has such a good attitude and he’s a great guy, but you will not find Mark at tons of events because he’s actually working on building his company. People tell me they haven’t seen me in a while – well, it’s because I’ve been working! Not that I’m anti-social, but I can’t go to every event going on and actually focus on building a business.

Malwarebytes operates quietly under the radar here. Their headquarters are in San Francisco, and nobody really pays much attention, but their guys here are going to work and building a business every day. Pilgrim built their company here, and you don’t find them out at every event either. Mayra Harley and her husband are building a new company and it’s doing very well. I love them and they’re great people, but the last time I saw Mayra was at TBBJ’s Women CEOs Roundtable. I have a better chance of running into her having dinner than I would finding her at an event. You’re talking about a company that has 25 employees after 2 years and is a pure tech company.

These are all people that are focused on the company, not on the activity. And you’ll find that it’s not just here. If you go to Silicon Valley or Boston, you’ll find the same thing there. People go out occasionally, but the majority of the people that attend startup events end up being students or people who heard that so-and-so was speaking at the event and they wanted to hear them. We also tend to have events that we say are for startups, but they’re not necessarily really for startups – meaning that the people who are speaking aren’t the people that a startup would care to hear about.

Full Stack Talent Tampa Bay Tech Leaders - Speakers

A poll came out recently along the lines of, “If we could bring anyone into town, who should we bring to get everybody to come?” I’m like, how about bring nobody? How about don’t bring somebody from out of town? Go find someone who actually built something real here. That’s the person that people should be looking at as an example.

We should bring people like Travis from Caresync in. I say this with the best of intentions. People will probably poo-poo that because of the failure with Caresync, but Caresync was not his first company, and Caresync employed many great people for a long period of time at far higher than the median wage in our community.

Joy Randels - Full Stack Talent Tampa Bay Tech Leaders - Startup Failure

We have to get over the fact that startups fail. Because they do, and it doesn’t mean the founder did anything wrong. Prior to that, Travis had built a highly-successful company. When people look at Caresync, it would be in their best interest to think about that. Every time Caresync raised, Travis put his own money in. You can look at the records, it’s all public through the SEC. He put his own money in, every step of the way. So it wasn’t like, “Oh, Travis blew someone else’s money.” Nope, it was a big chunk that he lost as well.

That’s why I think having someone like Travis coming in and speaking would be interesting. You’d get to see both sides of the equation. One company that’s wildly successful, and one where everything was going great, and then something happened. That’s how life works, right?

So to me, if we’re gonna talk to somebody, maybe we should talk to someone who built that here!

On TechNova, Ignite!, and Barcamp

Roxanne: I love that answer. Can you tell us a bit about your involvement with TechNova?

Joy: This is our 11th year. We are a 501(c)(3) non-profit. We put on day-of education events, but also 2 big events every year. Ignite! happens in the Spring, and BarCamp happens in the Fall. 100% of the content for both events is community-sourced. We do this for the community because we love it. We don’t even pay ourselves for gas.

BarCamp will be on November 10th at University Mall. This will be our 11th BarCamp. We did it at the USF campus for several years before, so this will be a little bit different. The other thing that will be different this year is we’ve never had themed rooms before, but we’re doing that this year! For example, we have quite a few people that are doing work in the cybersecurity space, so we’ll put all the talks that are cybersecurity-focused in their own room. Now that doesn’t mean that a sponsor will take 10 sessions and run 10 sessions in a room – it just means that this room will have a theme. If cybersecurity is your jam, you can go in that room, stay there all day, and hear one talk after the other.

We’ll also have a themed room for software development, and one for robotics and AI. There will be really cool stuff that we’re doing in that space this year.

BarCamp has a theme every year. Last year’s was our 10th anniversary, so that was a little funky. This year’s theme is Left Brain, Right Brain. We encourage everyone to come out. It’s 100% free, we give you breakfast, lunch, an afterparty, and a free t-shirt if you get there before they’re all gone! We have 500, so we have a good number, but we usually end up with 800 people, so…

All we ask is that people register at www.barcamptampabay.org, and if you want to give a talk, come give a talk! We’d love to hear you. There’s nothing really off-limits, other than no pitching. If you have knowledge you want to share about what your company does, you can source ideas. If you have a product concept and want to host a customer feedback session, you can do that – get people to critique your work. We have talks on everything from SEO to how to make an electric skateboard. All different kinds of stuff. It’s a fun day – there’s really nothing else like it.

Justin Davis just mentioned us on his podcast. He usually comes each year and gives a talk. Justin has First Chair Partners and Madera Labs here. He’s a front-end developer, UX design. He’s great.

Roxanne: I met him at Geek Breakfast that time I went. Good guy.

On finding a co-founder

Matt: To tie in with all the events we just talked about, one of the frequent questions I get at these events is from people very early in the startup stage. How do I find a co-founder?

One of the standard pieces of advice I give is: there are a couple different websites you can leverage to find yourself a co-founder. If you’re not technical but know what kind of tech stack you need, you should really be going to related meetup groups since that’s where you’ll find truly passionate people. Another site is angel.co. You can put up equity in the company as opposed to salary when it comes to job postings. What’s your advice?

Joy: I tell people to go to meetup groups and go to Geek Breakfast or Geek Lunch. The reason I tell them to go to meetups is because I think that the hardest thing isn’t necessarily finding technical talent, it’s finding technical talent that is also someone you can get along with. A lot of people go, “I want to find a co-founder and I’m going to give them 5% of my company.” Good luck with that! No one is going to bust their ass for 5% equity.

I tell people to go to meetups because a couple things happen. You’ll get to see their personality and how they interact with other people – so there’s that social aspect. And you’ll get to ask a lot of questions if you’re not too shy. Strike up a conversation. Say, “Hey I’m thinking of doing this, what would you recommend?” Most developers, even though some are primarily 1 or 2 disciplines, have a pretty good sense of different things. For example, Matt is one of those guys. And then Scott Olipra as well. I think it helps you vet your idea, find some holes in your idea, things like that.

I also tell people that if they’re not technical and they’re looking for a technical co-founder, they can approach it in a couple different ways. They can either do a try-it-before-you-buy-it kind of thing where they agree to what the terms would be and try it for 60 or 90 days. The other thing I do personally since I’m not a coder is that if I was looking for a technical co-founder, I’d contact one of my previous CTOs whom I am good friends with and ask them to vet the person for me. Is this person someone they would hire? So if you’re not technical, find someone that is so that they can help you vet the technical talent.

If you get someone who thinks what you’re doing is really cool, that’s different. This is something I feel many people miss when looking for a technical co-founder – they don’t necessarily look for the person who’s as passionate about the company’s mission as they are. And that’s where the problem comes in – because they start thinking, “Oh you’re just my technical talent.” But if you find that person that shares your vision, it’s much easier to negotiate. Maybe they keep their day job and they can spare 10 hours a week after hours until there’s money there to pay the person, or until they can afford to come in and work for straight equity.

On being The Startup Whisperer

Roxanne: Robert Trigaux put you in The 25 most influential business players in Tampa Bay as The Startup Whisperer. How do you feel about what he wrote about you?

Joy Randels - Full Stack Talent Tampa Bay Tech Leaders - Silicon Valley vs. Tampa

Joy: I didn’t even know about it at the time. Somebody sent it to me and said, “Hey did you see what Bob wrote about you?” and I went, “Uh… no?” So yeah – he called me The Startup Whisperer, which is pretty cool. When I read it, I thought it was awesome! People asked me if the article pissed me off, and I said no. He said that I was one of Tampa Bay’s biggest startup fans and toughest critics, and that’s absolutely true! Why would I be mad about that? It’s the truth.

We have some people building great businesses here, and we have some that are more – and this is probably more on the ESO side than the companies themselves – about touting what they’re doing and the value they bring to the community. I’m not saying ESOs shouldn’t exist, but the focus shouldn’t be on them.

I’ll give you a great example. In Silicon Valley, does anyone ever go, “What accelerator did you come out of?” “What coworking space do you work at?” “Have you been to a Startup Weekend lately?” I can assure you, those questions never get asked. “Tell me about the cool stuff you’re building.” “Have you gotten any traction yet?” “How much money have you raised?” “How much money do you need to raise?” “What’s your runway?” “Are you looking for more talent?” Those are the questions you get asked. So if we ask those questions, we solve the problem. And the ESOs still exist out there – there are plenty of accelerators and coworking spaces – they’re just not the main players.

It’s like the Brad Feld theory. Feld says, “Entrepreneurs must lead the startup community.” As soon as it’s not the entrepreneurs leading and it’s the ESOs and all the supporter organizations, you have a problem because it’s about them, not about the companies. VCs don’t come and the money doesn’t come to support ESOs. They come when there are enough real companies to invest in. That’s how you change the money equation as well.

Women in tech

Roxanne: Being a woman in tech, have you had to face any discrimination in the community? I’ve heard it from both sides of the fence. Toni Warren said she hadn’t faced much discrimination and that Tampa was a very friendly tech community. But I’ve spoken to other women who said Tampa is not very inclusive when it comes to women in tech. What’s your take on it?

Joy: In my career, I’ve had to face it – I just don’t really care because I don’t take no for an answer. If you want to know whether Tampa is inclusive or not, look at how many tech companies there are in Tampa, and how many of them have a C-level executive that is a woman. That’ll answer your question very quickly.

Roxanne: Not many.

Joy: Exactly. Less than the Silicon Valley average, which is 4.5% by the way.

Roxanne: How can we make tech in Tampa more accessible for women?

Full Stack Talent Tampa Bay Tech Leaders - Women in Tech

Joy: I think that’s up to the women. Honestly, I have a very different viewpoint on that. I think part of the problem is you don’t get to play the victim card, you simply have to go after what you really want and just don’t take no for an answer. I never walk into a room and think to myself I’m the girl so I’m not going to get x – I go into it thinking I’m going to get what I want. You have to adopt that mentality.

This is from a Stanford study: if a woman is going after something, whether it be venture capital or a promotion inside of a company, 80%+ of women will not even apply or go out and ask unless they believe they meet 100% of the qualifications. Do you know what that number is for men? Less than 10%. Guys just go for it. So you have to change the mentality. Don’t wear that chip on your shoulder – just go after what you want. If you don’t know all the answers, that’s ok, you’ll figure it out.

At the end of the day, female founders give a significantly higher rate of return to their investors than male founders do.

Michael: Can you speculate as to why that is?

Joy: I’ll give you 2 reasons. I do believe women are better multitaskers than men, so we have a tendency to put more things out there. We also, unlike men, put ourselves last. It’s kind of what you’re taught to do from the time you’re little – that caretaking role. I don’t think we do it consciously – we don’t go “oh I’m gonna put myself last” – but we go “all these other things have to be done so I’ll get to this other part later.” So you have a combination of those things that are just inherently part of who women are.

The other side of it is that women feel like they have something to prove so they work harder. It doesn’t mean guys are bad, and in fact, sometimes that singular focus that guys have is really beneficial from a leadership perspective.

Each person is going to be a little different of course, but if we’re generalizing, I think those are some things that are out there and that contribute to that disparity.

Roxanne: I’ll give you an example since we’re on this. You are the second woman we’ve interviewed so far, just because there are so few women in tech in the Tampa area. And for the ones that are, they’re usually so busy that they don’t have the time to do these interviews.

Joy: Oh I know… I know.

Talent in Tampa

Matt: Can you speak to how the talent landscape has changed when it comes to tech in Tampa? Is there better, more qualified talent in the area?

Joy: It has gotten better, however, I think that among the problems we have in our community, we have a lot of technical talent that doesn’t actually work here. They choose to live here because they like Tampa, but they work for a company outside the area, and they work remotely from their home office or out of a coworking space. We have really talented people, but the reasons they don’t work for companies here are twofold.

One, there aren’t as many pure tech companies here. Two, and more importantly, the ones that are here don’t want to pay market rate.

I get people telling me “the reason we’re here is because we can get development talent for $60,000.” Well, you won’t keep them, because there is somebody else who will pay more. If I’m a developer and I can make $150,000 working for a company that’s not here, or I can make $90,000 working for a company that is here, which company am I going to work for?

Michael: The one paying $150,000.

Joy: Right, because money is money. I might rather be here and go play foosball in the office, but if I can make almost double my salary working somewhere else, it doesn’t make any sense. It’s true for developer talent, it’s true for UX talent, and it’s true for IT talent. So if we pay right, we’ll be able to keep these people. We can solve a lot of problems by ponying up the cash.

Matt: Remote work is really making it difficult as well. It would be one thing if New York or San Francisco were paying Tampa rates for remote, because then at least companies here would be able to compete. But when they’re paying remote workers the same salaries as SF and NYC, shops locally can’t compete.

Michael: I can’t tell you how many developers I reach out to for work and they tell me “remote only.” At least 20% of people. Once they get used to that, that’s how they want to live.

Joy: If I’m a remote worker, I can sit at home in shorts and a t-shirt and no one cares. I can manage my time. If I have something I need to do in the middle of the day, I can go take care of that and make up the time that evening. It’s hard to compete with that.

Tech in Tampa

Matt: What do you hope to see in the next few years in Tampa Bay when it comes to technology?

Joy: I’m working on a project here in Ybor in the cybersecurity space, and I’d love to see more talent here. We lose so much. People will come out of school here and they move to DC or somewhere else. Not because the money is necessarily better, but because the work is more interesting. So how can we bring more projects here that are interesting to work on? We should be able to do that because we have SOCOM, we have JSOC, and we have private sector businesses. When it comes to cybersecurity, people don’t realize that only 10% of all the revenue goes to the public sector. 90% goes to private.

I think in some ways, SecureSet is helping with that. We also have ISC2 that is based here, we have a lot of SANS instructors here, and the largest SANS conference is held in Orlando. But I’d love to see more stuff in that, and I’d love to see the talent pool develop. That doesn’t mean from the university perspective, because like anything else when it comes to tech, there’s theory and there’s practical. Universities are great at teaching theory, but real practical experience, that’s a little bit different.

I’d love to see companies create some apprenticeship-type things locally. Like an in-between space for people coming out of those schools and programs to go and hone their skills in a real world scenario. That makes them more valuable employees here, and then there’s an incentive for that company to hire them on, versus losing them. I can give you a couple examples of companies doing that. SAIC does a lot of this in their locations. They take a lot of students out of Virginia Tech, and they bring them on during their junior and senior years – during the summer, as a paid internship – and they hire about 50% of those people, sometimes higher. Georgia Tech does the same thing with Coca-Cola in Atlanta on the technology side.

About 80% of those people get offered positions at Coca-Cola, and the majority of them stay. They’re very loyal. Coca-cola pays their employees well – not insane money, but market rate – and it’s a good company to work for. Plus, you get to play with the latest technology.

When you think about tech people, part of what moves us is being on the front end of that new technology, and playing with all that new stuff. The more opportunities we can give to people here to be on that leading edge, that’s how you’ll get more people to stay here.

Advice for those going into tech

Roxanne: Is there anything you’d like to say to anyone thinking of going into tech? Any words of wisdom from your years in the industry for college students or career changers?

Joy: The whole reason I chose this path is because I get bored easily, and technology changes every day.

Joy Randels - Full Stack Talent Tampa Bay Tech Leaders - Challenge

When I first started in this industry, I worked at Apple. I could tell you every single piece of software that was available on the market for a Mac. No lie. I knew everything about everything. I couldn’t tell you 1/10th of 1% of what’s out there nowadays. So to me, if you want something that’s going to give you the opportunity to challenge yourself every day and something that will give you the opportunity to leverage the newest things that people are thinking around the world to make the world a better place, it’s the best industry to be in.


Matt: Here’s the fun one. Who is a person and/or an organization that you think is doing something right and innovative in the area, and why?

Joy: There are 2 that come to mind.

Firstly, I’d say Kurt Long from FairWarning. They’re building a massive company that is changing how cybersecurity and privacy in that space work. Not only is it innovative, but they’re a force. Everyone I have met inside the organization is rowing in the same direction, and to me, that’s how you create real change.

The other is Susan O’Neal at Dabbl. They’re in the advertising space, but at the same time, they’re changing the equation for how you consume discounted deals and things like that. They’ve done an amazing job so far. Definitely innovative technology. They’ve raised the money they need to grow and to scale their business, and I have no doubt that she will build a big company here over time.

Final thoughts

Roxanne: Anything exciting coming down the pipeline for yourself or any of your projects?

Joy: It’s funny that you asked about the female issue. There’s a reason I had the figures on hand!

My personal opinion is that the best companies are the most diverse companies. If I look at myself, historically, my companies didn’t have all girls or all guys, and we didn’t have all one race or ethnicity. We had a mix.

People coming together who have very different viewpoints, if you can work together, allows you to solve a lot of the problems that I see startups face. Meaning they only look at one perspective. If I put 5 people in a room that are just like me, then we’re all going to say the same thing – and that’s really cool if you just want to hear yourself say the same thing over and over again, but it’s probably not the best plan.

I get asked about women’s issues all the time. I kept asking myself why is it that some women have been very successful and some haven’t? It’s not that their idea is bad or they’re not smart or they won’t work hard – so what’s the difference? I think it’s the attitude and the skills that you have. I’m the oldest, and I was a daddy’s girl. My dad told me to go after what I want and to never let anybody stand in my way. So I’m working on something to help other women scale their businesses. My goal is to launch that before the end of the year. It’s going to be a combination of a platform and a service.

Outside of that, there’s a new group that’s going to be in Ybor called the Undercroft. I’m part of the founding group. It’s going to be located in El Pasaje, right next to the cuban club – the old Sofwerx facility. This will be a cyber collaborative initiative with a focus on bringing like-minded people and companies together – those who are solving real cybersecurity problems today. There will ultimately be a non-profit associated with it to help put together scholarships for other people called Cybor. General Scott is also a part of that. He’ll be working on the public sector side and I’ll be working on the private sector side. You’ll probably see some stuff come out on that in the next month or so.

And again, BarCamp is going soon!

About Joy Randels:

Joy Randels is a serial entrepreneur and technology executive with a passion for launching and building high-growth businesses. She is a startup junkie, launching or helping launch 89+ companies, raising $357M+ in venture capital, leading 17 acquisitions of venture backed and/or bootstrapped companies, and two successful IPOs.

Joy is a thought leader and cybersecurity evangelist, frequent industry speaker including RSA, BlackHat, and SANS among others. She has been frequently quoted in SC Magazine, Wired, Red Herring, CSO, Information Week and other publications.

She is a technology executive with Fortune 50 and entrepreneurial expertise covering all aspects of business and serving in multiple CXO roles.

Roxanne Williams is the Marketing Director at Full Stack Talent, a technology staffing agency in Tampa, FL. Find her LinkedIn here.

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