CEO Connect with Harry Hedaya

For Tampa Bay Business & Wealth’s most recent “CEO Connect,” we had some very special guests—puppies. (See photos here)

But the star of the show was Harry Hedaya, TBBW’s February cover star.

Hedaya is a serial entrepreneur, based out of Tampa. He’s worked in industries like staffing, financial services, small business marketing and communications.

In his most recent role, he is chief information officer of Send It By Text, his third company, which helps businesses efficiently communicate with potential leads and clients.

His business ventures have a combined revenue of approximately $50 million per year.

Bridgette Bello, CEO and publisher of TBBW, interviewed Hedaya in front of a live, sold-out, audience at the Humane Society of Tampa Bay. This transcript of their discussion has been edited for length and brevity.

Talk about the best thing that has happened since your appearance on the cover of TBBW.

I’m 53 years old and when you go at a certain pace, it’s not often you have to stop and reflect upon the last 20, or 30, years. The best thing for me was sitting down in that conference room and thinking about all of the fun stories. You see your vision come to fruition.

Do you have any news to share since we did the interview?

My financial services business was approached with interest to purchase. At the end of it, we weren’t convinced that we wanted to sell.

I don’t know if it had anything to do with the extra publicity of the article, there were groups that were interested in buying us suddenly. We gave them a number, like ‘No way, they’re going to come back.’ And sure enough two groups came back with that number.

Of course, that has something to do with the article [laughs].

Maybe. [Audience laughs.] I still don’t know if I want to sell it. I love going to work every day and doing what I do. It’s a great place to be.

That’s exciting. For those of you that don’t know, there’s another star among us. I have to ask you what it’s like being married to someone who has 1.3 million followers, between Tik Tok and Instagram [referring to the Bunny Barbie]?

Well, aside from hearing weird sounds coming out of the closet upstairs … [audience laughs].

She does all of her videos in her closet. It’s pretty funny.

It keeps you young. That’s all I have to say about that. [Laughs.] It’s a good place to be.

She’s pretty popular, though. Is there anything coming up that you can talk about?

I think you guys are going to have to wait a while on that one.

OK, moving on … . How has the pandemic affected your business?

I always look at earth-shattering events as opportunities. I always have. I’ve been through a couple of them over the years.

When it first happened, it was unlike anything I’d ever come close to. I’m sure all of you can relate. The day they told us to go home and stay there until further notice. It was not a good time to be in business.

Will our customers pay us? Is our business model still viable? What’s going to happen? Is this doomsday?

It didn’t end up being like that. I would say the pandemic, in many ways, forced us to take a harder look at what we do and adapt to the change that the pandemic bestowed upon us.

At the very least, it has given businesses a reason to become leaner. In our experience, we had the opportunity to cut a lot of costs. Luckily, our leases came up halfway through the pandemic and we cut our office space in half, and half of the people are working from home.

I think if we can make it through this, I don’t think there’s a whole lot we can’t make it through as a business. As long as you’re willing to adapt, you are going to be just fine.

Do you think we will ever go back to needing the same amount of office space?

I was actually talking to a friend of mine and he works for a hedge fund. His specialty is real estate. He told me in the office space world, he would break it up into two categories. There are the brand new projects, like Midtown and Water Street, he said he thinks those will do phenomenal because people will pay that premium to fit whatever it has, especially post-pandemic, into that sort of real estate. Those places are going to do good.

Some of the other places will have to reinvent themselves to compete with that. I think that’s when, as some of these leases come up in one year, two years or three years, you’re going to have companies realizing that they don’t need the kind of space that they used to.

How do those spaces reinvent themselves to fit into what we call the “new normal?”

I don’t know what the answers are. I’m not in the commercial real estate business but I think that it will be very segmented. That some stuff is going to do amazing and other stuff is going to have to figure out what’s their new purpose.

If a mall that was built in the 1980s can figure it out, office space can figure it out.

What motivates you? What keeps you going? What keeps you wanting to start another business?

At the core, what gets me up and out of the bed every day, and really excited, is solving problems. My whole business career has been one of solving problems, and finding solutions, that other people may not think about.

What I’m really excited about is now I get to do that for other businesses. That’s something that’s brand new to me. I’ve always done it for myself.

I want to give you the opportunity to talk about Send It By Text.

People are tone-deaf to voicemail and email, even answering the phone. Especially the younger generation. Send It By Text was born out of the need to actually have communication with people and get the message across in a convenient fashion.

You’ve been through a lot of recessions and you were pretty inspiring in the interview. Would you talk about that?

We have not really seen a recession [currently] yet. We’ve seen a difference in the way we work. Inevitably, the economy is going to go up and it’s going to go down. That really doesn’t matter. At the end of the day what matters is providing value.


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