Kiki Roeder has been an active part of the Tampa startup community for the last few years. She has founded and exited two companies and is the Director of Women Who Code in Tampa. She was happy to share her knowledge and wisdom with us in this interview.
Roxanne Williams: I’d like for you to tell us a little bit about Punctuate. When is the platform launching?
Kiki Roeder: Punctuate is an EdTech marketing solution that empowers people to monetize their expertise. Most organizations and businesses create incredible content for their website in an effort to convert customers. These can be swipe files, courses, lead magnets, videos, etc. Punctuate provides a plugin and marketplace so businesses can generate more leads and land more conversions through the content they’re already creating. We are in private beta with customers and doing well, and wexpect a public launch in late spring. Right now it is about listening to the needs of our users. We’re in testing mode, but making profits. It’s going fairly well and we’re excited about it.
Roxanne: As the Director of Women Who Code Tampa, I’m sure you’ve heard your fair share of horror stories when it comes to women in tech. What are some things that we, as individuals, can do to make the tech community more inclusive?
Kiki: A more inclusive work environment starts with leadership. Too often, diversity and inclusion efforts fall to Human Resources or the Diversity Officer. Companies can see it as checkmark of what they are “supposed to do,” rather than as a necessary solution to address corporate culture as a whole. It’s important to create a culture across the organization that is open to all backgrounds and ideas. You can institute this by re-evaluating how meetings are conducted, how goals and progress are measured, instituting inclusive hiring practices, and communicating values of openness and transparency across the organization.
Leaders can also re-evaluate traditional working models to serve people with ranging schedules and backgrounds. Flexible work hours and remote work can often make it easier for working parents, for example, to be a part of a tech community. Additionally, remote teams often allow for ideas to flow from people from across the country or even world. In a remote workplace, from my experience, success is more likely measured by performance and not office politics. No matter what a company chooses to do, an inclusion strategy needs to be at the forefront of creating not only today’s tech teams but companies as a whole.
Roxanne: Have you experienced discrimination as a younger woman in tech?
Kiki: I have. My most incredible mentors have been men, though. I think that instead of calling men the oppressors, we must create a better dialogue so that they understand what’s happening in the workplace. Every time that I’ve done that, I’ve had a fairly good experience.
Very early on in my career, I worked for a massive tech company in Seattle. I had an incredibly bad experience there, in terms of the amount of discrimination I was experiencing. It made me leave tech for a while. It wasn’t until 2 years later that I started to create my own ideas and path, and that’s what led me towards entrepreneurship. I felt like I was on an “adulthood plan” my whole life in thinking that I had to graduate college and then get some big corporate job. But when I left that corporate career, it ignited the spark to create my own thing.
I’ve experienced inappropriate advances and touching. I’ve had men say things to me that have been condescending. And, I’ve had them assume that if I designed something, I must have been in charge of the colors rather than the technical aspects. But I’ve also had men that have stood up for me and championed for me.
I think the biggest thing women can do is create those dialogues. “Hey, what you did there, talking over me in a presentation, that came off as you disregarding my input. So, please understand that.” And a lot of times, most men are like, “Oh, I didn’t even realize I was doing it.” You have to speak up first and move on from there to challenge discrimination.
Matt: You mentioned being pushed towards the entrepreneurship route. Can you tell us about your past experiences, including Startup Sisters?
Kiki: Startup Sisters sparked through an effort with my co-founder, Stephanie Jewett. She’s the founder and CEO of Activvely, which is a fitness app out of Atlanta. She and I connected and became friends. We saw that there was a great need for female entrepreneurs looking to connect with other women founders. It first started out as an ad hoc group of women meeting together in Atlanta, but now we’re in three markets. We started in Tampa last year from the Startup Week stage. In the last year in Tampa alone, we’ve had hundreds of women attend our events.
Through Startup Sisters, we’ve been providing opportunities for women and their allies to be part of conversations about how to lead and build better companies. It’s been really great. We’ve done tons of workshops. Anything from accounting, to PR, to social media, to increasing sales and hiring your first talent. It’s just been really wonderful, and we’ve been so surprised by its growth and how many people have come out for it.
Matt: Going into your own entrepreneurship, tell us a little bit about what being an entrepreneur has brought you. Are there any common pitfalls you would suggest others avoid?
Kiki: The party line is that I’ve built and exited 2 startups in the last 5 years. The first startup was an EdTech company that I sold to a very large technology company when I was just 27 years old.
I transformed a grad school project into a thriving startup, which sounds easier said than done. The hard part is that during that phase of bootstrapping my business, I literally put everything on the line. I was sleeping in a really crappy apartment, putting everything that I was earning into making that business happen.
When you’re in business for yourself, you see money very differently. A lot of times, you’re thinking, “This $500 can go towards a marketing campaign.” Or, “If I save $5,000, that can help me hire a contractor so that I can level-up my project management.”
I was very, very lucky at the time that I had a “sponsor” by also working full-time at the same time to make it happen. It was probably the most intense period of my life. I barely slept for 4 years. Gained a whole bunch of weight and got really sick. I put my body through hell to make it happen, but obviously, I do have a success story there.
I think a lot of founders don’t realize that 9 out of 10 startups fail. There’s a very high level of risk when you’re building something from scratch. You have to go all in, but you also have to be smart and know when you have to kill projects, pivot your business, and know whether or not something is working.
When I first started my company, I’d never conceptualized the word “entrepreneurship.” I never knew that was even an option. And now, many kids want to be entrepreneurs when they grow up. For me, it was a little bit different.
A lot of people think that they need to have a lot of followers or that they need to have this big brand presence, but I think the most important thing when you’re an entrepreneur is to be building really great relationships with your customers. If you have the love of your customers, you pretty much have a successful business. Instead of focusing on venture capital and having these dreams of millions of dollars from VCs, I think it’s more vital to think about building a business that makes money. If you can make money, all the other stuff is going attract and work in your favor.
After I sold that company, a couple of years later, I created a marketing and digital strategy studio. We served clients across four continents. We grew very fast, and within a year, we sold that company. That development process was the opposite. The first company was really a business where I just wanted to see it exist. It was a project I just wanted to see realized. The second one was like: this is an issue that I know I can solve, and I know that there’s a market for it. So we built this company, and within a year, we found a buyer for it. It was a totally different process.
But again, it was very stressful. I’ve been building and tinkering and dealing with burnout and waiting to find my next big project. It’s been a journey.
Matt: You kind of skipped a step. A lot of founders will do what you did, working full time until it gets to a point where then they can quit and do that full-time. However, you were still working a full-time job when you ended up getting acquired.
Kiki: While I was in grad school, I was also working for a university full-time. I had access to incredible resources, which made it so much easier for me to test and scale projects. And I think in that situation, I was very lucky, in terms of my full-time job also being something that supported the goals of my startup work as it applied to my research.
Matt: Nice. We don’t hear a whole lot of side-hustle success stories that make an exit.
Kiki: Sometimes, you have to leverage what’s going to make it work for you. It was an incredibly stressful time. I would literally get up in the morning every day at 3:30 or 4:00am, check all of my emails and set our PM goals, and then go to my regular job. Once my day job ended at 6:00pm, then I’d be working until 1:00am managing all the operations and the other stuff. I’d be flying across the country on weekends to make things work. It was a very crazy time. But it allowed for us to support my co-founder as the West Coast presence we needed to make things happen.
Roxanne: Speaking of craziness, are there any particular “oh shit” moments that stand out for you?
Kiki: “Oh shit” moments always happen. I remember we did this big email campaign very early on. We had built our list up, we were going to share this new product, we were just about to elevate the ask, and the link that we sent in that big email campaign was dead.
Roxanne: Oh nooooo!
Kiki: Even the exit was something that we didn’t plan. It happened as a total surprise for us, and it was tough to transition from the mode of growing a business and then seeing it shift: “Oh, this baby that I’ve put my whole life into, seemingly, is not going to be mine anymore.”
That’s a challenge, and I think people think of the success story in the end being this great triumphant moment of when you’re running across the finish line in a marathon. You see the glory shot of the hands up, but you don’t see the nausea, the blisters, and all the other stuff that goes on to get to that point. So, there definitely are “oh shit” moments constantly. You just have to be able to move forward with it.
And it’s okay to cry in the bathroom, men and women both. I’ve seen my co-founders get in that zone where it’s like, don’t talk to them for a while, bring them some Cheetos and some coffee, and just back out of the room slowly. When shit hits the fan, a lot of times you just push forward, and the only thing that helps is setting your goals and having a very clear understanding of what your ‘why’ is. If you don’t have that ‘why’ and it’s not integrated into the culture of your company, it’s really going to affect how your team performs. You have to make sure everyone’s on the play and everyone’s acknowledged.
Matt: What’s something that is generally considered to be a pro of entrepreneurship that might not be as great as everybody thinks it is until they’re doing it?
Kiki: Obviously, when you get to be your own boss, that’s amazing, right? But then you have to be your own boss. When the day ends, you can’t really say, “I’ll see you tomorrow.” The idea that you can just shut it off at 5:00pm and then start the next morning, I don’t know if that’s even possible. From my experience and from every entrepreneur I’ve ever met, when you’re your own boss, it’s amazing. You get to set the direction of your life. But at the same time, one of the hardest parts is not associating the way that you feel about yourself to the success of your company.
I also think new entrepreneurs think that it’s quick money. It’s not. A lot of times, it takes 18 months at least. And for a good chunk of people, there are 6 months when they’re pretty much either eating through their savings or asking friends and family for money.
You’re putting it all in, and, if you are coming from the security of a job or the security of something else, you have to be willing to understand that financial security may be challenged dramatically.
I’ve seen people eat through their savings and then they don’t have anything at the end. You have to be comfortable with that, because there’s a high level of risk. Again, when I was building that first company, I was literally sleeping on the floor. Everything I was putting into my life was put into that business. I’m not suggesting that everyone live that way, that’s just the experience I had.
A lot of entrepreneurs are what I call “wannapreneurs.” They want the perception of it. They get on Instagram and they do their rants in their stories. But you start asking them about what their business’ value proposition is, or what they actually build, or what they provide for their customers, they can’t answer you because they’re not actually making money, they’re just creating buzz.
The biggest thing with being an entrepreneur is that you have to ask people constantly. If you’re not comfortable asking people to invest in your product, to buy your service, for your employees to give their time to you when you can’t pay them the same salaries that a big corporation can; if you’re not comfortable asking and putting yourself on the line to make your goals happen, then it’s going to be really hard.
Roxanne: We’ve run into you now at two Startup Weeks. What led you to get involved as an organizer?
Kiki: I had just sold a company before moving to Tampa and was looking to connect. I love startups, I love businesses. Business is kind of my sport. Some people can talk all about football. I can talk all about startups, so I was looking for a way to do that.
The first organization that I interacted with was Startup Week. I thought, “Seems like they did a really good job. I would love to be involved in some way.” And I think it just kind of went from there. I’ve met so many incredible people. I have really great friends that I met through Startup Week and through Startup Tampa Bay. They put on one of the best Startup Weeks I’ve been to.
Roxanne: You spoke earlier about burnout. How do you get over burnout personally? What do you do to take time to recharge and all that? And also, to give some context for people that might not know everything else you’re involved with, what projects do you have going on? You’re teaching a class for Suncoast Developers Guild now, correct?
Kiki: Yes. I’m slated to be teaching a 6-week part-time digital marketing course for people of all backgrounds to become savvy at digital strategy. I’m really excited about it. Toni over at Suncoast is amazing, and I’m a huge fan of her. I really believe in what she’s doing, in terms of trying to build a developer community in Tampa. Teaching is something I very much enjoy doing, and am happy to give back, if I can.
To burnout, I really wish I had a great answer for that right now. But I’m definitely into the thick of it, having just put on Startup Week (which took 6 months+ to organize). February was so intense. Startup Sisters had 5 events that month. We’re in the middle of a product launch for Punctuate. Everything was hitting at the same time.
I think the best thing I would suggest people do, and what I constantly hear, is definitely go outside. For me, if I take a walk and I listen to a podcast like Masters of Scale with Reid Hoffman, I find a little bit of center. It really helps me just to be outside in nature.
I think other people probably have better burnout management. If I’m honest, I feel like I’m definitely on the threshold of it right now. I probably shouldn’t be saying that on the record, but it’s just one of those things. Entrepreneurship has peaks and valleys. You’re constantly going up and down and up and down.
I think what helps me, too, is scheduling my time. I pretty much schedule my entire day: emails, calls, meetings. When you’re in the thick of it, if you don’t have a schedule, it really can mess up your flow and actual productivity.
That’s a downer answer, but I am the happiest I’ve ever been in my life so at the same time. It’s a challenge for anyone. They always say you shouldn’t hustle harder, you should work smarter. I think that’s also part of it, too. How can you be more efficient with your time and with your output? You don’t get a badge for being busy. Being smart with how I manage your time, I think, is the best thing to help with burnout.
Matt: We’d like to get your thoughts on the shift in tech talent in Tampa. What kind of trends you have seen in your time here? Does the Tampa market satisfy your personnel needs?
Kiki: I hate to say this, but I’ve actually been shopping for talent outside of Tampa. I’ve had a hard time finding developers at the level they need to be. Or they’re working for big corporations like Tech Data and the Raymond James, and less likely to take the risk of joining a startup.
There will be more talent to go around with the rise of coding schools like SDG and other programs that have been popping up through LaunchCode and Computer Coach. They’re helping to elevate the talent here for startups and the business community in general.
Also, with the coming of Embarc Collective, the fact that we’re getting national attention from the Rise of the Rest tour, and all of these other entrepreneurial organizations, I think there’s going to be a bigger push for talent in the region. These opportunities are providing a gateway to the Tampa community.
Roxanne: Out of curiosity, you mentioned having trouble finding devs of a certain expertise. What is it exactly that you have trouble finding? Advanced PHP, Golang, Ruby on Rails?
Kiki: Yeah. The challenge is finding devs who truly know app development, not just the drag-and-drop blanketed tools. They actually know how to code it. They know the emerging stacks necessary to make dynamic apps. There’s a lot of .NET in this town. It’s just been a challenge for what I’m looking for.
I’d love to find those who are really able to move fast in the Agile development process. And that’s, again, exposure. It’s either training or where the talent is coming from – traditional dev and software jobs – in corporate environments versus startups.
I hate the fact that I’ve had to look for talent outside of Tampa Bay, but I think the talent will change here with the amount of university programs, vocational training, and startup attention that is developing in this market.
Matt: What are some ways to find mentors, like yourself, that want to try to bring people up? For a lot of younger tech folk, it’s hard to find a true mentor that’s looking to help shape them. What’s your advice around that?
Kiki: You can’t find a good mentor in a vacuum. Go to meetups, attend events, connect with people, even if you’re an introvert weirdo like me. If you go to those things, you’re eventually going to find people that you’re going to want to learn from.
I think the biggest thing is, if you admire someone, tell them and ask for some time. Most people won’t be a jerk to you if you’re kind about it. So, asking is the best way to find a mentor. Get comfortable with LinkedIn and sending cold emails and putting your hand out there with a polite and enthusiastic ask.
Matt: Excellent. And also, don’t say introvert weirdo like it’s a bad thing! Normal people are boring!
Kiki: No, I’m proud of being an introvert weirdo. Ha. I’m okay with it. Sometimes, I come off way too formal, but that’s because I come from a corporate and academic background. But yeah, I’m okay with flying my flag!
Roxanne: What do you hope to see in the next few years in Tampa Bay when it comes to technology?
Kiki: I’d love to see more of the tech community being united. As a transplant, it seems so strange to me how divided this community is in St. Pete versus Tampa. I’d love to see more dialogue happening.
There’s all of these great new programs that are happening at UT and USF. I think in a couple of years, the conversation about what technology looks like in this city will be very different. I think that the startup culture will be very different, too. What I’m hoping for is more developers in town, as well as more realized startups and exits.
Matt: Any words of advice that you would give to anybody thinking of going into tech and, with that, maybe even specifically the women who might be scared to step into the tech world?
Kiki: The most incredible thing about tech is that there are so many ways to develop and find your own voice within it. You could be really into backend, frontend, AI, machine learning, the data side of it, the product management side of it. Just stepping into it, there’s always going to be a niche for someone in tech. It’s unending, so just try it out. If you’re interested in learning something, go to a meetup and ask dumb questions. Most of the time, people are going to be super nice about it.
I think from a woman’s perspective, connecting through women’s groups really does help. You can learn new skills and learn from others’ experiences. Seeing other people do it, excelling at it, and sharing their voice empowers you to think you can do it, too.
Women are often afraid to ask, or they’re afraid to put themselves into positions where they don’t hit 100%. I think it really helps to see, “No, you just have to give your best and you’ll find your own place.” Many of these organizations help with that.
Roxanne: Who is a person or an organization that you think is doing something right and innovative in the area outside of your projects, and why?
Kiki: I’m really excited about what Embarc Collective is doing. I’ve been to a few of their events. They flew someone in from Chicago to do a sales training a couple of weeks ago and the dialogue that they’re having really excites me. I love what I’m seeing from them, and the fact that they’re going to help the tech community by exposing it to resources within and outside of Tampa Bay.
Matt: Any further thoughts or insights you’d like to share? Anything exciting coming down the pipeline that you want to highlight?
Kiki: I just hope that people will get more involved. There are lots of great opportunities to forge your own path in Tampa Bay. Whether its Startup Weekend, where you launch a business in 48 hours, leveling up your learning at Startup Sisters’ events, or attending any of the coding meetups in town. This area’s totally bubbling with awesomeness. It’s a good time to be in Tampa Bay.
Kiki Roeder has built and exited two companies. She is on the eve of launching information product marketing solution, Punctuate.
Enthusiastic about helping entrepreneurs and businesses reach their full potential, Kiki contributes to media publications, Fortune 500s, and startup organizations across four continents.
Kiki is currently the co-founder of Startup Sisters USA, as well as a regional leader with Techstars Startup Week/end and Women Who Code.
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