Entrepreneur Florida Tampa Bay What I’m Up To

I’m going on StartupBus again, and you should too!

After the great interruption of 2020 and 2021, North America’s largest, longest-distance hackathon, StartupBus North America, is back for 2022! From July 27th through 31st, 2022, seven buses will depart from seven locations across the continent…

Tap to view the map at full size.

…and make their way to Austin, Texas in three days. During those three days, “buspreneurs” — StartupBus’ term for its participants — think up and build a tech startup from the ground up: the idea, business plan, software, and pitch.

One of the seven buses making its way to Austin over three days is the Florida bus, and it’s leaving from Tampa. This year, one of the Florida bus’ conductors — StartupBus’ term for its coaches/facilitators — is…Yours Truly!

🚨 Keep reading: later on in this article, there’s something that I’ve never told anyone online until now.

I was on StartupBus in 2019

Me on StartupBus Florida, shortly after we pulled out of Tampa.
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I was a “buspreneur” on the Florida StartupBus in 2019, the last year the event took place, when the destination city was New Orleans. Along with my teammates Rina Bane, David Castaneda, Justin Linn, and Tracy Ingram, we made it all the way to the finals and got the runner-up position.

Team Hyve! From left to right:
Tracy Ingram, David Castaneda, Joey deVilla, Rina Bane, Justin Linn.

The startup we created on the bus was Hyve, a service that lets you create virtual disposable email addresses that you can use when subscribing to services or communicating with untrusted people.

My whiteboard diagram showing a use case for Hyve.
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Rather than provide a service or person with your real email address, you use Hyve to generate a disposable email address to give to that service or person, and it forwards emails sent to that disposable email address to your real email address.

What happened on StartupBus Florida 2019?

It started with a get-together the day before we boarded the bus, which was captured in this ABC Action News piece:

Our ABC Action News piece. Tap to play.

As you may have guessed, we spent a fair bit of time coding and designing the service…

Tracy, Rina, and David at work.
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…but at the end, we present our startups to panels of judges, so we also spent a lot of time working on our pitches. We did so many practice pitches on the bus, followed by feedback from the conductors and our fellow buspreneurs, including this one by Tracy:

Tracy Ingram pitches Hyve to our busmates.
Tap to play.

Just as startup life is full of unpredictable events, StartupBus is designed to mirror that unpredictability. For starters, we only knew that the destination was New Orleans, and that it would be a roundabout one so that it would take three full days. I pieced together the route shortly before we arrived:

StartupBus Florida’s 2019 route from Tampa to New Orleans.
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We knew that there would be stops at night for hotels as well as other places, but we didn’t know where or when.

Our first non-meal/gas/bio-break stop happened in the late afternoon of Day 1 when we visitied the Entrepreneurship Garage at NC State University in Raleigh, North Carolina. It let us get more work done in a stationary place with access to more guidance, better internet connectivity, more reliable power, and (very importantly) bathrooms. It’s where we recorded this mandatory “Why are we on the bus?” video at the end of Day 1…

Meet the Hyve team.
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…and it gave us a chance to refine our pitch by trying it out on non-bus people, such as the Lyft driver who took us from the Entrepreneurship Garage to our hotel:

Pitching Hyve to our Lyft driver.
Tap to play.

Day 2 gave two buses a surprise: upon our departure from Raleigh, the Florida and DC buses merged to become the Swamp Thang bus!

Boarding the newly-merged Florida/DC bus.

Now we had a full ride:

The newly-united Swamp Thang bus.
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We got to know the folks from DC, and the spirit was one of “coopetition” — we knew we were all competing against each other, but we also made friends and even helped each other out. I ended up spending a little time helping a DC developer with a bug in their Flutter project.

We had a stop at Advent Coworking in Charlotte, North Carolina, where our bus met up with the New York bus, and some of us (time was limited) got to do our first pitches in front of a panel of judges.

One of the teams pitches at the stop in Charlotte.
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There were also the “unexpected unexpected” events — the unexpected events that the conductors didn’t plan. There was the time our bus got stuck on one of the oversized speed bumps at NC State:

Usually, we say “we’ve run into a speed bump” only figuratively.
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The solution: Unload the bus completely — after removing all the people and luggage, the bus was able to clear the speed bump.
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Our big “unexpected unexpected” happened when the bus overheated and had to pull over on the highway somewhere in the mountains in Tennessee:

Stuck on the mountain in Tennessee.
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This delay meant that getting to the next stop meant staying on the bus well into the night:

Into the night.
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Day 3 was a long, hard drive with a lot more pitching, designing, coding, and reaching out to prospective business partners and customers (yes, you have to treat your bus startup just like a “real” one!), but at long last, we arrived in New Orleans:

Finally in New Orleans!
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Which brings us to Day 1 of two days’ worth of pitch competitions: the qualifiers.

At the qualifiers in New Orleans.
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All our previous pitches were mere rehearsals. This pitch would determine if we would get into the semifinals!

Our qualifier pitch in New Orleans.
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Our qualifier pitch in New Orleans.
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Here’s our qualifying pitch:

Our qualifying pitch. Tap to play.

We continued working into the night of Day 1, refining the code and pitch. We wouldn’t find out who would make it into the semifinals until Day 2 — and we did!

Announcing the semifinalsts in New Orleans.
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So we worked on our pitch and code, bringing in Andrew Romaner as a consultant (remember, you’re running like a real business, so you can get consultants if you have the connections!)…

Getting some help from Andrew.
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…and made it to the finals!

We made the finals!
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So we worked some more…

A quick selfie break before getting back to work.
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…which led to our final pitch:

Our final pitch. Tap to play.

Once all the finalists made their pitches, the judges sequestered themselves, and shortly afterwards, they made their announcements, which included Hyve!

Announcing the winners. Tap to play.

Just because I love that bit about walking the line between good and evil, here’s just the part about Hyve:

“There’s a thin line between good and evil.” Tap to play.

Here’s the reporting on our victory:

The reward for our efforts

Let me be very clear: StartupBus offers no prizes of any sort. No cash, no prizes from sponsors, not even a trophy or certificate. In fact, you’ll spend money in the process, including getting home (the bus gets you to the destination city, but you have to make your own way back).

So why do it? Because what you gain from StartupBus is more valuable in the long run than mere coin or prizes: experience.

It’s one thing to be an employee working from home or in an office. It’s an entirely other thing to be a startup founder — even for less than a week’s time — collaborating closely with people you’ve known only for hours, on a bus, where the power and internet are unreliable, and dealing with the curve balls that the conductors and the vagaries of the road will throw your way.

Something I’ve never told anyone until now

There are more comfortable things that you could do with your time, but I remind you that the magic happens outside your comfort zone.

Here’s something I’ve never said online until now: I was fired from my job in June 2019. But rather than cry in my own beer and wonder how I’d explain it to prospective employers, I decided to shake things up.

My plan was simple:

  1. Join StartupBus, which was happening in July 2019.
  2. Winning or at least be a finalist.
  3. Parley the victory and experience into my next job or a new company.

Simple? Yes. Easy? Most certainly not. But extraordinary outcomes need extraordinary effort, and StartupBus definitely falls in the “extraordinary effort” category…

This picture takes on deeper meaning after you read the next paragraph.
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…especially since one of the judges in the finals was the CEO of the company that fired me. We’re on good terms, but if I can pitch under those circumstances, I can pitch anywhere, anytime, anyhow. I knew it was going to happen if I made it to the finals — in fact, I was counting on it.

“Guess who’s back / Back again…”
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StartupBus gave me the opportunity to gird my grit, sharpen my software skills, and polish my personal pitch. I’ve taken my experience on the bus and used it to get to the rather nice place where I am today.

After StartupBus, I contacted Trey Steinhoff, a buspreneur from 2017. He and Robert Blacklidge created Course Align, which grew into a real business beyond the bus. Trey was Director of Product at Lilypad at the time, and they were looking for a mobile developer.

Me and an ad for Lilypad in an industry magazine, shortly after my first bug fixes to the Android version were released.
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“Why just take on any mobile developer, when you can get one who’s also been on the bus?” I asked, and got hired. It turned out that Akira Mitchell, one of the conductors on StartupBus Florida, was a scrum master there! I remember telling Akira “You know, it’s so much easier working with you at actual desks in a stationary office than on a bus bouncing all over the road while the wifi’s going in and out.”

I also cited my StartupBus experience during my interview process with Auth0, where I now work.

I got to go places I’d never seen or place I hadn’t seen in a while. I got to get to know some friends better, and made new ones with whom I’m still in touch today. I got to experience a challenge that most techies don’t take on, and I boosted my “personal brand” at a time when I really needed that boost. StartupBus can pay off big if you harness the experience.

And now, I’m a conductor

Posing with some Humvees that we spotted on the final hours of the bus ride.
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A couple of weeks ago, I was contacted about being a conductor. “Your name keeps coming up, over and over again, so — would you like to be a conductor?”

I still have more to experience and learn, and this time, I’d like to do it by helping, mentoring, and guiding buspreneurs on the Florida bus. I owe it to the Tampa Bay and Florida tech communities that have given me so much. And hey, after all this time cooped up, I’m ready for some new road adventures.

Are you on the bus?

This is probably the most important slide they show at the finals.
Tap to view at full size.

As I write this, we’re less than 100 days away from the day the bus leaves Tampa for Austin. The question you should be asking yourself is:

Are you going to be on StartupBus? The Florida bus will depart from Tampa, but there are others leaving on the same date:

  • The Advancing Black Entrepreneurs bus is one especially for a greatly underrepresented minority in tech, and it departs from Cincinatto, Ohio.
  • The California bus’ departure point is yet to be determined.
  • The Latinxs in Tech is another bus for another greatly underrepresented minority in tech, and it departs from Miami, Florida.
  • The Mexico bus departs from Ciudad de Mexico, a.k.a. Mexico City.
  • The New York bus departs from New York City?!
  • The Texas Bus departs from San Antonio, Texas, and yes, they’re going to plan a route that takes three days.

You can’t just sign up for StartupBus — you have to apply, because we’re looking for people who are determined to create a great startup under sometimes-gruelling conditions and give it their all.

To register, you’ll need to visit StartupBus’ “Apply” page and enter an invite code. Of course, you’ll have to enter an invite code, and you just might get one if you tweet @TheStartupBus and explain why you’ve got what it takes to be on the bus!

Entrepreneur Florida What I’m Up To

Videos from StartupBus Florida 2019

I recently found the video above, which features an ABC Action News story that covered the “Welcome” party held for StartupBus Florida participants on the evening before our three-day bus trip across the southeastern U.S.. It’s been two years since that extended long weekend in late July 2019, and while COVID-19 ended any possibility of safely holding then event in 2020 and 2021, I hold out hope for a StartupBus return in 2022.

The 2019 edition was the 10th annual Startup Bus North America competition, which might be describes as “Shark Tank goes on a road trip”. It’s a competition that takes place on a bus ride where contestants (better known as “buspreneurs”) form teams, ideate, and come up with an innovative technology startup, then build a working application — all in the space of three days. While on a bus.

I could go on about what the team and I did, but I’ll let these videos tell the story instead…

Meet Team Hyve!

Here’s our first team video, which we recorded at the end of Day One of the bus trip at NC State in Raleigh:

Pitching Hyve to a stranger

One of our assigned tasks — on top of building a startup and the application that powered it — was to pitch our idea to a stranger in one of the towns where we stopped. We pitched the Hyve concept to the Lyft driver who took us from NC State to our hotel. Here’s how it went…

Practicing our pitch

In addition to building the business and the app on the bus, each team on the bus practiced their pitches at regular intervals by presenting to their fellow buspreneurs. Here’s Tracy Ingram from Team Hyve delivering our pitch as the bus raced towards New Orleans:

The qualifying round

The qualifying rounds took place on Saturday, July 27th at New Orleans’ Propeller Incubator, where all the teams from all the buses — the Advancing Black Entrepreneurs, Florida, Mexico, New York, Ohio, Silicon Valley, and Washington DC teams — made their pitches.

Every member of every team had to be ready to pitch, because in the qualifying round, the judges chose two people from each team to make their pitch, one at a time. They tend to choose the least confident-looking team members, and a couple of them already knew me. We did well, though, with Rina doing the “set ’em up” pitch and Tracy doing the “finish ’em off” one:

The finals

We’d have to wait until the next day to find out who made it to the semifinals, but we were among them! Even better, we made it to the finals. We re-worked our pitch for the finals judges with the help of the Florida Bus Conductors — Akira Mitchell, Nick Price, and Shane Needham — and here’s the result:

The winners

Once all the finalists made their pitches, the judges sequestered themselves, and shortly afterwards, they made their announcements, which included Hyve!

Just the bit about Hyve

Just because I love that bit about walking the line between good and evil, here’s just the part about Hyve:

Current Events Entrepreneur Tampa Bay

“Funding Florida’s Growth”: Thursday, Aug. 12 at Embarc Collective

On Thursday, August 12th from 5:30 p.m. – 7:30 p.m. at Embarc Collective, TiE Tampa Bay will host Florida’s Office of Financial Regulation Commissioner, Russell C. Weigel III in an event titled Funding Florida’s Growth. It will include a networking reception followed by their special guest speakers:

As the event page says:

The goal is to promote Florida’s economy by creating a self-sustaining, in-state capital market where many newly formed businesses can obtain seed or expansion capital. The desired outcome is to have Florida residents and businesses receive capital from within our state and ultimately remain in Florida and contribute to the state’s economy.

Visit the event page to find out more or to register for the event!

Entrepreneur Tampa Bay

Tampa Bay’s tech startup future is female-led

Photo of Tonya Elmore, Lakshmi Shenoy, Jill St. Thomas, Rachel Feinman, and Linda Olson
From left to right: Tonya Elmore, Lakshmi Shenoy, Jill St. Thomas, Rachel Feinman, and Linda Olson.
Photo by Amy Pezzicara for Tampa Bay Business Journal. Tap to view at full size.

While the U.S. technology landscape is by and large defined by young, straight white men, almost every Tampa Bay hub that supports technology startups is run by a woman:

These women recently participated in a “virtual sit-down” interview panel with Tampa Bay Business Journal, and the result is their article, The Future is Female-Led.

As its tagline says, “Almost every major startup organization in the region is led by a woman. They’re setting a tone that will have a ripple effect across the entire tech ecosystem.”

If you’re wondering what the Tampa startup scene is like, you’ll definitely want to read this article.

Entrepreneur Tampa Bay

Find out more about Tampa’s tech and startup scene

If you want the most up-to-date overview of Tampa Bay’s startup scene, you’ll want to check out Startup Guide: Tampa Bay.

Dan Holahan, member Experience Manager at Embarc Collective.

It was just published yesterday, and it’s written by Dan Holahan of Embarc Collective, a startup accelerator/incubator/coworking space located near downtown Tampa.

Dan’s writeup covers:

  • A quick summary of “The Other Bay Area”
  • Tampa Bay’s capital landscape
  • Notable Tampa Bay startup fundraising deals that took place in the last six months
  • Tampa Bay’s startup funders
  • Tampa Bay startups to watch
  • Local incubators, accelerators, and startup hubs
  • Coworking spaces in the area
  • Tampa Bay tech/entrepreneur conferences
  • Tampa Bay community and event organizers
  • Local tech media and podcasts (and I cover more in my recent article on Tampa Bay tech podcasts)
  • Local startup job listings
  • Tampa Bay city initiatives aimed at entrepreneurs

The Latest on Tampa’s Tech Scene was published in October 2020 and features a number of Tampa Bay-based entrepreneurs, organizations, and activities, including:

Here’s a video showcase 50 innovators and companies making their mark in Tampa’s tech and startup scene:


Here are a couple of articles showing how well Tampa rates against other startup hubs around the world:


Want to know more about what companies in Tampa Bay are worth watching? These two articles are a good start:


You need two key ingredients to build a startup scene: nerds and rich people. I’ve pointed you to articles about the nerds, so here’s one about the rich people who’ll fund the nerdery:

Need more convincing that Tampa Bay is the right place for your tech startup? These might help:

Current Events Entrepreneur Tampa Bay

Tampa Bay tech startups in 2020 are busy raising money (and what’s in it for you)

Photo: Tampa Bay scenery superimposed over a big pile of money

Even in the middle of a pandemic, Tampa Bay tech startups in 2020 are busy raising money, having raised over $200 million so far this year.

Logo: deepwatch, a Tampa Bay tech startup

The really big deal was made by St. Pete-based deepwatch, which provides “cloud-first” managed security services to a number of Fortune 500/100/25 companies. Goldman Sachs led this Series B investment for $53 million.

Logo: Telepathy Labs, a Tampa Bay tech startup

Earlier this year, Telepathy Labs, who are in stealth mode and whose product is some sort of “predictive and adaptive conversational agent”, raised $6.6 million in early stage funding, and St. Pete Catalyst reports that there’s been a $14 million investment in them in Q3.

Logo: Immertec, a Tampa Bay tech startup

Immertec, whose product is a Unity-powered VR surgery training platform, raised $12 million in an early-stage Series A.

Logo: IMCS Group, a Tampa Bay tech startup

The IMCS (Integrated Medical Case Solutions) Group, who develop solutions for injury/trauma prevention and work-related injuries,  received an $8 million capital infusion.

Logo: Kliken, a Tampa Bay tech startup

I’ll admit it — as an old D&D player and fan of Clash of the Titans, I can’t resist a good “Kraken” pun. That’s why I like SiteWit’s new name, Kliken. Their service lets you integrate marketing campaigns in your site, and they raised $6 million in a Series B.

Logo: Homee, a Tampa Bay tech startup

Homee, the home construction/contractor service platform, got a $5 million early-stage investment in July.

Logo: SKUx, a Tampa Bay tech startup

SKUx, based in St. Pete, creates one-time-use digital incentives to get customers to spend more at retailers. They raised $4 million in angel funding.

Logo: Covercasa, a Tampa Bay tech startup

Covercasa’s offering is a platform for searching for and buying home insurance. They raised $1 million in angel funding.

Logo: Blockspaces, a Tampa Bay tech startup

And finally, the blockchain development studio Blockspaces, where a lot of local blockchain-related meetups are held, raised $75,000.

“Okay, so these Tampa Bay tech startups in 2020 got some money. What’s in it for me?”

For starters, all this investment activity helps raise the profile of these Tampa Bay-based tech startups in 2020, which in turn helps put Tampa Bay on the tech map. This helps to push the narrative that “The Other Bay Area” is a great place for techies, entrepreneurs, and nerds in which to live, work, and play.

Also, there’s the matter that this money is meant to grow these companies, which in turn means new job openings. If you’re looking for work in tech, you’ll want to check out these companies’ sites and see what openings they have.

Current Events Entrepreneur Tampa Bay

St. Pete Pitch Night: Online tonight at 5:00 p.m.!

St. Pete Pitch Night takes place online tonight from 5:00 to 6:30 p.m.! See pitches from five St. Petersburg entrepreneurs as they compete to win up to $5,000 by pitching their community-based businesses.

From the 34 business who applied, these were the ones selected:

  1. Eat Your Words Custom Cookies
  2. Eventron
  3. Oh Yes! Shave Club
  4. Jun Cyber
  5. Cope Notes

To be eligible, contestants had to meet these requirements:

  • Scalable and/or innovative concept
  • In business for 4 years or less
  • Previously presented at 1 Million Cups OR currently enrolled in an entrepreneurship program at a Tampa Bay college or University

Admission to attend this online event is $5.00. You can find out more about St. Pete Pitch Night on the St. Petersburg Chamber of Commerce site or the St. Pete Greenhouse site, and you can register to attend St. Pete Pitch Night here.