David Segura – Sometimes Slowing Down Can Keep You Alive

Mar 1, 2022

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BIO: David Segura is an accomplished entrepreneur and investor. He currently serves as the CEO of Glassbox Media. This podcast platform enables Podcast Hosts to grow their brand revenue and new listener base with direct investment and technology support.

STORY: David invested in and joined a startup in New York. The company was growing fast, and after their Series A funding, they got convinced by the lead investor to expand to London and other international cities prematurely. The company could not sustain the growth.

LEARNING: Be deliberate with your growth plans. Focus on quality growth that you can build on.

“Be deliberate with your growth plans.”

David Segura

Guest profile

David Segura is an accomplished entrepreneur and investor. He currently serves as the CEO of Glassbox Media. This podcast platform enables Podcast Hosts to grow their brand revenue and new listener base with direct investment and technology support.

David previously founded Giant Media, serving as the CEO from launch through acquisition. The company was an early Video Advertising Exchange that included AMEX, L’Oreal, and Dollar Shave Club clients. David launched the company in 2009, and an AdTech roll-up acquired it in 2014.

David is also an active startup investor with upwards of 60 investments.

Worst investment ever

David got interested in a startup company based in New York and invested in 2017. He believed that the genesis of that business was terrific, and the founder was brilliant. The founder even convinced him to get on board as an investor and as the chief strategy officer.

The company was doing well in New York, and they decided to expand to other cities. To do so, the company had to raise funds. They raised $12 million in their Series A, and the lead investor was British, and they wanted the company to devote a lot of that capital to expand into London as soon as possible. The data indicated that they should double, even triple down in New York and not expand internationally. David tried convincing the founder that expanding internationally was not a strategic decision and they should instead push back. But they didn’t. They just went with the flow and used a significant amount of the capital raised to expand internationally. Not just London, but other places as well. The fast growth was too much for the company, and it couldn’t handle the capacity.

Lessons learned

Be deliberate with your growth plans. Sometimes it’s prudent to slow it down to be more sustainable.
When investing in a startup, it’s ok not to know what you’re doing or be a little scared.
Identify the problem holding your business back and solve it. If you keep ignoring the elephant in the room, you’ll regret it.

Andrew’s takeaways

Growth, in and of itself, is not everything; it’s got to be quality, growth that you can build on. The growth that goes beyond the capacity of the operations to deliver what you’re promising is not good.
Whenever you’re expanding, locally or internationally, take the time to look at the risk and return.

Actionable advice

Whether you’re the founder, an angel investor, or even a VC, continually evaluate what the company is doing. Be honest with the senior executives and yourself and figure out ways to minimize risk. A lot of times, that means just focusing and narrowing down.

No.1 goal for the next 12 months

David’s goal for the next 12 months is to grow Glassbox Media into a US household name that creators and podcast hosts think of when they need help to scale their audience and revenue.

David Segura – Sometimes Slowing Down Can Keep You Alive

Guest profile

Worst investment ever

Lessons learned

Andrew’s takeaways

Actionable advice

No.1 goal for the next 12 months

Connect with David Segura

Andrew’s books

Andrew’s online programs

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