The Inaugural 2019 Triangle Tweener Celebration and Awards Event — Highlights and Pics!

Scot Wingo
9 min readFeb 12, 2019

On January 23rd, 2019, we hosted the first annual Tweener List Celebration a the North Carolina Museum of Natural History (aka the dinosaur museum). I’ve been working on this Tweener idea since 2015/2016 and it was really rewarding to take Tweeners to the next level by hosting the first ever (and hopefully not the first and only) Tweener event. In this post, I wanted to share the highlights of the evening and most importantly, the winners of the 2019 Tweener Awards.

You could say we had a WHALE of a time…

How the Tweener Event Was Born

At ChannelAdvisor, for the last 10+ yrs, we have hosted an annual event called Catalyst that is half customer meet-up and half industry event. Suffice it to say, I have a very clear and deep understanding of what it takes to put an event on, so over the years when folks have said: “Scot, you should do a Tweener event!”, I have shied away from it. Fortunately, lady luck raised knocked on the door around Thanksgiving of 2018. I was approached by the Friends of the NC Museum of Natural History about a tricky puzzle — how could we partner to bring the startup and tech folks in the Triangle into the museum, build awareness of this awesome area asset and get them excited about what’s going on?

I was intrigued enough to go and see the space, because it had been 4–5yrs since I was there with my kids. I was immediately blown away by the uniqueness and feel of the space. Plus, there’s a really interesting vibe that lives at the intersection of startups and dinosaurs. Dinosaurs are a stark reminder of how fast the world changes and the importance of evolving to stay on the top of the food chain. Everyone in the startup world knows that yesterday's predator is tomorrow’s pray if you lose a step.

I was sold on the space, but the next challenge was figuring out how to sponsor the event. Fortunately, two firms I’ve worked with over the years had already said: “Hey if you ever want to do a Tweener event, let us know”. I pinged HPG and Robinson Bradshaw and we locked in the date for 60 days later. The scramble was on to not only make sure the 2019 Tweener list launched on time, but to find all the CEOs’ contact information and invite them along with other folks from the Triangle startup ecosystem to the event.

Thanks to the hard work of the great folks at NCMNH, HPG and RB, we pulled it all together and on January 23rd hosted 150–200 folks that included the sponsors, Tweeners and Entrepreneurial Ecosystem.

As someone that has written about the ~150 companies on the Tweener list, but never met a pretty big chunk of them, it was really awesome to meet everyone and to be able to introduce the 2019 New Tweener class, while celebrating the successes from 2018.

Awards Recap

There were five categories of awards, detailed below, to save space in this post, I won’t go over what the companies do or their history, but you can find it all in the tweener list here.

Note: DNA indicates that a representative was not able to attend the event (Did Not Attend).

Top Tweener Exits

With $200–$400m in exits for 2018, it was a banner year. The winners for the 2018 Top Tweener Exits are:

Racarie Software- acquired by Swipeclock. Racarie’s CEO, Nathan Shackles was there to accept the award. Congrats again Nathan!

  • Sageworks, acquired by PE firm AKKR (DNA)
  • TransLoc, acquired by Ford (DNA)
  • InmotionNow, acquired by PE firm Level Equity (DNA)

Congrats to the winners and thanks for showing that the Triangle is definitely high on the M+A hunt list for not only the top private equity (PE) firms, but also large corporations looking for innovative, rapidly growing companies to add to their portfolios. Note we also have a lot of IPOs, but nothing of note in 2018 as the IPO window was largely closed.

Top Tweener Fundraisers

In addition to a strong year of exits, 2018 saw over $200m in new venture funding for Triangle Tweeners. There were three winners in this category:

  • PrecisionHawk: $75m round (DNA)
  • Pendo: $50m round (DNA)
  • Teamworks: $15m round. Teamwork’s co-founder and COO, Mitch Heath was there to receive the award:

Top Tweener Buzz/PR award

One of the 2018 highlights for the Triangle startup scene, in my humble opinion, was the appearance of our very own Triangle startups on Shark Tank.

Therefore, Jonathan Hayes, with Rewardstock won the Top Tweener Buzz award for bringing fire to the tank and his awesome representation of the Triangle startup scene!

If you haven’t seen Jonathan’s performance on Shark Tank, it’s season 10 episode 5 on your favorite streaming platform.

Most Promising New Tweeners

With about thirty new additions to the list this year, it was incredibly hard to pick a handful to put into a ‘most promising category’. But based on the experience of the founder, the size of the opportunity and investor interest, I picked these four winners of the Most Promising New Tweener award:

  • Infinia ML — CEO, Robbie Allen (DNA)
  • Real Magic/Levitate— Jesse Lipson (DNA)
  • Pureport — Rich Lee. Rich is a serial entrepreneur who started Hosted Solutions and sold it for > $300m. He’s back with a really cool new company in the cloud infrastructure space called Pureport. This is definitely a Tweener to watch:
  • Silbo — CEO: Brendan Szulik. I’m an e-commerce marketplace guy, so when I first heard the pitch for Silbo (a marketplace in youth sports for leagues to find referees), I was hooked and have been mentoring Brendan+Silbo for a couple of years — plus Brendan is a pretty big Star Wars nerd, so we have a lot in common :) They raised a $1.3m round in 2018 which was a huge accomplishment. Startups are a grind and Brendan+team have been really grinding it out (getting punched in the face, falling down, getting back up, rinse-and-repeat), so it’s really great to see them finally get the recognition the reserve. Stay tuned to Silbo, more great things are coming.

Class of 2019 New Tweeners

We split the new ‘Class of 2019’ Tweeners into two chunks (minus new companies that have already had awards)

Here is the first group:

  • Bee Downtown — DNA
  • Boostopia — Boostopia CEO Justin Winter was there to receive the award:
  • Carpe Lotion — Carpe lotion co-founders: David Spratte and Kaspar Kubica were there to receive the award (and I can 100% attest their hands were NOT sweaty, but ahem, mine may have been a tad sweaty).
  • DataClarity — DNA
  • Device Magic — Device Magic’s CEO, Dusan Babich was there to receive the award:
  • Diveplane — DNA
  • Element451 — Element451’s CEO Ardis Kadiu was there to receive the award:
  • FeedTrail (sorry did not get a picture on this one, but CEO Paul Jaglowski was there to receive)
  • Freedom — Freedom’s CEO, Fred Stutzman, was there to receive the award:
  • Hip Ecommerce — Hip Ecommerce’s CEO, Mark Rosenberg, was there to receive the award:
  • Imangi Studios — DNA
  • Improved Nature — DNA

The second batch included:

  • MemberHub — DNA
  • Mindsumo — DNA
  • Pawboost — Pawboost co-CEO, Tim Kijewski was there to receive the award:
  • ProAxion — DNA
  • ProcessMaker — ProcessMaker CEO, Brian Reale, was there to receive the award:
  • Proficient Auto — Proficient Auto CEO, Robert Koencamp was there to receive the award:
  • Pryon — Pryon CEO, Igor Jablokov, was there to receive the award:
  • Restaurant Furniture Plus — Restaurant Furniture Plus’ CEO, George Deeb was there to receive the award. George is also a partner in Red Rocket VC that has a great newsletter for startups I strongly recommend here.
  • Roobrik — Roobrik’s CEO, Nate O’Keefe, was there to receive the award:
  • Shark Dreams — DNA
  • StrongKey (they have a really cool octopus logo — check it out) — their CEO Jake Kiser, was there to receive the award.
  • ThinQ — DNA
  • Wiser Systems — last but not least (and as a Wingo, I have some experience here at the end of the alphabet), Elaine Rideout, CEO of Wiser Systems was there to receive their award:


After the event, the NCMNH head Paleontologist, Lindsay Zanno, PhD gave us an awesome talk about some cool fossils and everyone nerded out on 66,000,000 old dinosaurs.

Shout outs and Thanks

Thanks again to the NCMNH, HPG, Robinson Bradshaw, the awesome folks of the Triangle community that really showed up and Spiffy’s Kelsey Sullivan who ‘volunteered’ to be the photographer for the evening.

After Party: Crowd Shots!

It wouldn’t be an event post without some shots of the crowds — who can you spot from the Triangle’s startup community?

Finally, who is this rogue college kid hitting the food hard?

What’s Next?

It’s hard to think about another event after you just finished a heavy lift, but the feedback so far on the event has been very positive. What do you think — should we try it again next year? Let me know in comments. I like the idea of moving around the Triangle to different very unique places that you wouldn’t normally think of for events. Any ideas there?

Finally, let me know if you find any new tweeners out there or if you have ideas on how we can support these ~150 companies that are on their way to becoming the next Red Hats!



Scot Wingo

CEO of Spiffy ( and Co-Founder/Executive Chairman of ChannelAdvisor