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coLab Member Spotlight: Jonathan Whiting from StreetText

Created in 2010, StreetText provides easy Facebook advertising and lead generation funnels to help entrepreneurs grow their businesses consistently.


Today I met with Jon Whiting, StreetText co-founder and coLab member to get an inside look into his background and insights surrounding his entrepreneurial journey.

Link to the full interview here.


coLab: What inspired you to start your own business?

Jon: That’s a great question, and an interesting one. It makes me kind of think way back to the first time I started a new business (a clothing company). And for me at that time it was all about risk. It was about doing something where I was thinking, “Okay, you know this is sort of what I had, like I sort of had a plan and a direction of my life” that I thought, “okay, that would make sense, I’d become a lawyer…” or whatever the direction was, but there was an aspect where I was sort of putting it in a box, which was design and creativity and I just kind of shoved it down. And so I thought, “you know what, why don’t I just try it.”

Just try starting something that is focused on design. And I was really scared off because I thought what would people say at that time about a guy starting a clothing company, you know? 

I just was really afraid. And so when I’m so I did it, it was a big risk for me.

It ended up doing really well, and in two years it grew really fast and by December, it was the busiest it had ever been. And I created it just to take a risk, and to check the box, like it was so successful in my mind; I had an online store and I’m selling to clients or people are buying from the States and Australia.

And so I shut it down in the heat of its busiest. It was 2008, and I shut it down and I was like “Okay, good job. I know it worked”. 

So then the next business I kind of came out of there was a natural evolution of that, where I was trying again to do the traditional thing; I put out a bunch of resumes to apply for jobs. And while I was waiting for some responses, I wasn’t getting any.

So I ended up getting a lot of people contacting me and saying, “Hey, could you do a design for me as well?”. So I had a band contact me about making a poster. And then that just opened up a whole web design part of the business. before I knew it, I was so busy with that I had some cool clients come out of there. 

I had a national nonprofit woman clothing shelter with some really fun projects. I enjoyed doing it, and it was so exciting to help people with whatever they were trying to do. At the time, my brother was a real estate agent, and we connected and he was talking about starting this web platform to advertise open houses.

We could see there was something there, but I think we could see it as a bigger opportunity in front of us instead of a project. So we decided, with another friend (Art) that we should do this together. We all jumped in, and we didn’t know exactly what just going to be, just that we were going to build something.

That was 2009. Street Text has had its own journey to pivot. I’m really glad that we’re partners; we’re co-founders.

For me, it’s always been about taking a risk and also feeling good about what we are doing.

We are always learning, but are we really helping our clients succeed and putting them first? Are we creating the kind of culture and business that we would want to see modelled in other businesses?

Business is such a creative space; you can do anything you want.

It doesn’t have to be so restricted; it’s good to have focus and clarity about where you’re going because you get there a lot faster. 

But there’s a lot of freedom in that so you can kind of create the team and the culture and the environment that you really want to see in the world.

So I think it’s just so much opportunity. It’s more than starting an idea just putting it out there. The idea actually encompasses the business itself, as I think if you spend as much time in this environment as you do with your family, it’s an important amount of time in the day. Therefore, we have to be intentional with the kind of environment we are creating.

coLab: What do you enjoy most about being an entrepreneur? 

Jon: The ability to really create what you envision.

I think that’s it. There’s a lot of benefits that can come from it. But you have to be really intentional with them. Any project you do can become really all-encompassing. 

One of the benefits of being a co-founder is having a business partner (my brother) so that you can keep each other in check – It’s like two horses pulling a cart versus just one. I think being an entrepreneur is all about working with others, and that’s part of what makes the journey worthwhile.

It’s like if you travel and you go by yourself it’s exciting. But when you do it with other people it’s way more fun. 

coLab: I mean for me personally I’ve travelled on my own, but I met people while I was there too. So yes, it’s totally different. I’ve never been completely on my own, but it does make for a totally different experience.

Jon: I am the same way. I went to Switzerland myself and I ended up spending the whole time with the same group of people, and that is what made it so much fun.

coLab: It is a different story getting to work with someone else and share ideas with you.

Jon: You’ve got to appreciate and respect your partners. Because they are going have ideas that are different, or counter the way that you think. It’s really important to realize that just because we’re living in the same mountains, we might be looking and might see something the other person misses and keeping that open mind, especially when things are stressful as it’s critical to creating that healthy relationship. 

Having that shared experience. Otherwise, it could just as easily become a bit of a drudgery working with someone else because they may not see things the way you see them, and then you feel like there’s always a frustration of trying to share your perspective and they just don’t see it yet.

So you’ve got to pick the people you work with very wisely. 

coLab: What advice do you have for early entrepreneurs?

Jon: Just do it. The earlier the better. 

Like Einstein for example….all of his great theories; he pretty much had every single one of them before the age of 22 while he spent the rest of his life trying to prove them. 

So the earlier you do it, the better. I think our minds are so alive and awake when we’re young.

Jonathan Whiting from Street Text


And being an entrepreneur is an easy way to do that because you’re constantly training the mind to stay awake, thinking about the market of tomorrow.

Things are always changing and going so the earlier the better. The longer people wait, the more they want to build up a nest egg for security, but now they have something to lose. Whereas when I started the business I never had a nest egg. None of my businesses did. 

So I say just do it. So often people hold back as they don’t have all the specific answers.  You have to just figure it out as you go and start learning. There’s no other way to go about it.

There’s that famous quote which is “luck is what happens when opportunities meet preparation” and that kind of makes it sound like you’ve had to have prepared ahead of time. But I think preparation in that aspect is preparation of the mind in staying open.

Richard Branson said, “the best way to learn is to learn as you go”. It’s like people give us opportunities, and then just knowing that you’ll figure it out as you go.

In our company, the best analogy I can think of is it’s like jumping off a cliff and then trying to build an airplane before you hit the ground. 

And we had we came so close to the ground. 

I think you have to enjoy that process and just letting go and not holding on too much.

And for the early entrepreneurs, every moment you go through is an experience to learn something, even our greatest failures. I believe there should be no regrets in life. 

Even if we do think things like “oh, I wish I hadn’t done that”, or “I wish I had done this instead”. Those were all valuable learning experiences.

It was all meant to happen. 

coLab: I heard on a podcast recently, “failure is on the same path as success.” They’re not two separate things. It’s like failure just brings you closer to success. 

Jon: Another example is Dave Ramsey; he’s now built a huge business of a hundred employees. He said “The only difference between myself and someone else, is I’ve failed just as many times. I’m simply standing on top of my failures rather than allowing them to stand on top of me.”

You’ve got to stay open. 

The other thing is I’d say is to throw out your timelines.

I had these hugely unrealistic expectations of timeframes. I thought “in one year, we’d have a thousand customers”. 

I had to learn how to get rid of these unrealistic expectations, and the faster I did, the easier it became. Then I started to see the progress we were making.

coLab: I feel like once you accept that you can’t control everything and you don’t have such a huge death grip on it, it just happens much more naturally.

Jon: Then you start to make real momentum and learn from it, then start to build and say “okay, well that I can do again,” so that it becomes repeatable. 

coLab: What academic qualifications do you have, and do you believe they were beneficial career-wise?

Jon: I have a degree in political science with a minor in philosophy, and I spent the majority of my time at least in the early years writing and programming.

Totally different fields. I think that academics is one of those things where you’ve got to study what you’re passionate about, and it is no different in business.

It’s not worth it to do it strategically because strategic is boring. Be strategic of course, but study what you’re passionate about because that’s something you’ll actually learn, and take that with you. And then you’ll be able to apply that in whatever you’re doing because your brain will pick out the key aspects. I think learning and having people skills helps develop discipline. 

I didn’t have discipline. But when I finished university, I had academic discipline.

That discipline benefited me greatly, and there are skills you pick up along the way that are transferable. At the same time, you don’t need a specific degree to do anything in business. You can hire good accountants, you can hire good people who can do bookkeeping, you can hire smart people that are experienced in video marketing. There is always someone who can do it for you.

Knowing what certain classes I need for my degree is useful. But I think it’s vital to just do what you are passionate about; you never know what’s going to be transferable later on, and they all transfer. 

We live in an interesting culture now, and we see on the media especially that comedians enjoy bashing students for going to university. For instance, Conan O’Brian said, “congratulations for graduating, and now that puts you in only 92 per cent of all people to graduate with university every year…so much further than the other 8 per cent who didn’t graduate”.

The value for education can not be understated because even smart entrepreneurs that I meet, and I think they start these incredible companies in California and Chicago, and you know that they are driven by their desire to learn; as soon as they stop learning, they seem to lose their passion for business. 

Maybe Mark Zuckerberg didn’t need a degree to start Facebook, but I guarantee you that 99% of every person he hired had a degree because he couldn’t get the funding he’d need otherwise. 

I think university is much more important than most people realize.

I don’t think there was a right or wrong answer with that. It’s all what you make it, and how you use it. So the one thing I would like to just add that I think is important is that with the company Street Text, it truly is a partnership between myself and Steve. We are business partners, and we’re 50/50 in that.

I think the rewards are incredible because you have to trust each other. But then also be willing to respect when you have different opinions on certain things, or if they aren’t ready to make a decision right now. And sometimes that feels like you’re going slower than you have to, but in reality, you’re going so much faster because you build that culture of trust.

What happens is that when your team grows, you start to treat everybody in the company as a partner. Start to say, “well, what are your thoughts, what are your aspects, what are your what are your perspectives.”

We are a very intelligent team, and I think that leveraging that intelligence is so worthwhile. But oftentimes, a business can fall into the trap of trying to become efficient, and then people are hired purely for their brains.

But I think that if your vision and the strategy are both singular, then what you’re starting to operate in the same kind of unity as a sports team. And there are so many people involved in that. You can start to move things forward, but that requires a lot of communication. Overall, you will have a much better strategy in the long run.

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