Triangle Tweener Fund Adds Robbie Allen As GP, Makes 14 Q2 Investments

Serial entrepreneur Robbie Allen—who founded, built and and sold Durham-based Automated Insights—will now play a key role in Scot Wingo’s Triangle Tweener Fund. 

Allen is joining Wingo as a General Partner to help the Tweener Fund scale its mission to invest in Triangle early-stage tech startups, the pair announced today. [We first wrote about the Tweener Fund’s initial investments in January, and last month we covered the unveiling of the 2022 version of Wingo’s accompanying Tweener List, which inspired the fund.]

Wingo and Allen initially met 15 years ago, and Wingo served on the board of Automated Insights. After that, Allen joined RTP-based machine learning/AI startup Infinia ML—founded by a group of Duke data scientists—as its CEO. He’s also been a frequent GrepBeat presence as the host of our For Starters podcast and a former Q&A subject.

Wingo said now was the right time for Allen to come on board. After the fund’s first quarter in operation, there are more investors than expected and even more opportunities to invest than anticipated, Wingo said. When Allen reached out offering his help, Wingo jumped at the chance.

As an angel investor, Allen has made more than a dozen investments, and he believes there is great power in a Tweener-type directory and fund.

“It’s hard to pick the winners,” Allen said. “Even after having started a few companies myself and helped a bunch of companies, it’s just really hard to know which ones are going to be the ones that are the breakouts. So when he came up with a Tweener Fund and said, ‘Hey, why don’t we take an index approach and invest in as many companies that fit this profile as we can,’ that made a lot of sense to me.”

Now that Allen has joined the team, the pair say they will be able to recruit more investors, track potential investments and build out a tech infrastructure for the fund, given Allen’s background in software development, AI and machine learning. While machine learning and AI have yet to be fully incorporated into VC or early-stage investing, there could be high potential there.

“For me, it’s sci fi, but Robbie can actually go figure out, is there a bear there? And how do we figure it out?” Wingo said.

Along with this news came the announcement that the Tweener Fund made 14 new investments in Q2. This represents more than $800,000 invested over the quarter, bringing the total to 25 portfolio companies and over $1.4 million since the Tweener Fund launched in January of this year.

The new investment additions include ArenaCX, Offline Media, Chekhub, The Convoy, RepVue, Hip Ecommerce, Pattern Health, Quinsite, InsightFinder, Viably, Klearly, Diveplane and Reveal Mobile. [The links are to any previous GrepBeat coverage of those startups.]

Given the challenging current macroeconomic environment, it’s a good reflection of the Triangle tech ecosystem to see so many area startups still raising capital and achieving revenue milestones, Wingo said.

Allen remains confident that many startups will emerge from widespread economic troubles even stronger. 

“It’ll be interesting to see how things go over this next year if the economy continues to have some hiccups along the way,” Allen said. “But even if that happens, I’m still bullish about startups in general. There’s a lot of great companies that were built in the financial meltdown of ’08-’09.”

One of them was Allen’s very own Automated Insights.

“Even if we do have a bit of a downturn, it’s not something that scares me in terms of the overall startup community,” Allen said. “I think that can, in some cases, be a way to bring entrepreneurs back down to reality and make sure that they are focused on building sustainable businesses.”

Moving forward, Wingo hopes the Tweener Fund can invest in even more companies because the demand is so high. And investors are already lauding the fund’s diversified portfolio approach, he said. In the future, the Tweener Fund looks to increase its average check size beyond its current level of roughly $50K while providing guidance and mentorship to the portfolio companies that need it.

“It’s not just the money,” Wingo said, “but it’s our ability to help the Tweener Fund portfolio companies that also helps accelerate the flywheel.”

About Suzanne Blake 362 Articles
Suzanne profiles startups and innovation for GrepBeat. Before working at GrepBeat, Suzanne attended UNC Chapel Hill, obtaining a degree in journalism and political science. Previously, she wrote for CNBC, QSR Magazine, FSR Magazine and The Daily Tar Heel.