Entrepreneurs are Everywhere Show No. 25: Nigel and Vaughn Caldon and Kerry Frank

Tenacity and resilience. Getting people to buy in to your startup vision takes a thick skin, perseverance and willingness to learn. You’ll probably be laughed out of several boardrooms along the way.

Entrepreneurs refuse to take no for an answer.

The latest guests on Entrepreneurs are Everywhere shared what they learned from having their ideas rejected and how those lessons propelled their businesses forward.

The radio show airs on SiriusXM Channel 111 (weekly Thursdays at 1 pm Pacific, 4 pm Eastern). It follows the journeys of founders who share what it takes to build a startup – from restaurants to rocket scientists, to online gifts to online groceries and more. The program examines the DNA of entrepreneurs: what makes them tick, how they came up with their ideas; and explores the habits that make them successful, and the highs and lows that pushed them forward.

Nigel Caldon

Nigel Caldon

Joining me in SiriusXM’s studio in New York were

Vaughn Caldon

Vaughn Caldon

Listen to the full interviews with Nigel and Vaughn and with Kerry by downloading them from SoundCloud here and here.

(And download any of the past shows here.)

Kerry Frank

Kerry Frank

Clips from their interview are below.

Nigel and Vaughn Caldon are brothers who founded the startup The Street Academy for Financial Literacy and now BallStar togetherVaughn served as Associate Director of Alumni Affairs at Prep for PrepNigel spent five years working in investment management at Goldman Sachs and Citi Alternative Investments before going in to business with his brother. Nigel also teaches Data Analytics at General Assembly NYC.  

In building their companies, the Caldon brothers have found that when things get tough, there’s always a way to make it work.

Nigel: … We’ve done a pretty decent job … bootstrapping with limited resources — trying to figure out different ways to get work done and move the needle without actually spending any money. … There’s always a way and as long as you’re paying attention you’ll always be able to find some sort of resource that’s there to fill exactly what you need done.

Vaughn: You have to love learning… because some of the ‘no’s’ we’ve had have taught us more about the business than, you know, some of the, “Hey, I’d love to be a part of this.” 

Steve: Give me an example. Tell me about a ‘no’ that made you smarter.

Vaughn: You know, any ‘no’ from an investor that said, “traction” really meant, ‘I don’t understand your idea, but go ahead and try and prove it to us.’ … also someone who said, “You know, XYZ is this doing better,” or “We use this.” They put us onto a competitor that we didn’t know about. That wasn’t a ‘no’, that was a huge misstep on us not knowing this company was in our space.

Steve:  What happens when someone says, “Take a look at this competitor”? What do you do?

Vaughn: You’re in a better position when you know what it is because you don’t have anything and they’re stuck with what they have. That’s really inspiring me to go after what’s already out there.

If you can’t hear the clip, click here.

Kerry Frank co-founded Comply365 in 2007 with her husband. The company has transformed the aviation industry by replacing pilot flight bags with tons of manuals with digital tablets in cockpits.  

She struggled early on trying to get customers to see her vision for maintaining aviation manuals and other records on the cloud rather than on paper:

Kerry: Just a couple short months after that final testing (of Comply’s 365 product using a Kindle) the iPad came out and I looked at that. so I said, “Geez, I got to go with the iPad because look at this dynamic color and all of this.” I started running around to all the airlines with either a Kindle or an iPad and saying, “We’re going to change your business, we’re going to revolutionize the way you work, we’re going to take all the paper off the plane, we’re going to save you this much money.” I was laughed out of every boardroom.

… They said, “You’re way too innovative, we’re too risk adverse, we’ll never do this, you’re crazy, come back in a decade.” 

… I just continued to say, “No, you don’t have to be a legacy. You don’t have to have that “you can’t change” mentality; you guys can change. Anybody can change. You just have to believe it and we can revolutionize aviation. We can change the way we work and this will be safer. It will be the best for aviation in the long term.” I even went to top charting vendors in the world and said if you do electronic charting … 

Steve:  Like Jeppesen?

Kerry:  Yeah, laughed out of their boardroom. They said, “We’ll never do an iPad.”

Steve:  Are they on the iPad now? 

Kerry:  Yes they are.After a year of persevering, it was tough. We’re living on 50 bucks a week, a family of five (with the business) in the basement of our home. We have some employees, and we never missed payroll and we’re trying to change the world right? We’re trying to change industry. We got our first win and then our second win, and then within 16 months I had pretty much flipped the market.

If you can’t hear the clip, click here.

Focusing on your vision is critical, Vaughn Caldon said:

There’s so much that you want to do and then there’s what you have to do. I think the biggest learning curve is how to be in focused on that straight line. … because there’s something going on over here that you’d love to be involved and have your name next to it … may not be as important as another hour kind of vetting the design with someone you’ve been through it with a hundred times already.

It’s just really about focusing on what’s clearly the next step in front of you. That’s been the biggest lesson for us because … we were quick to bounce around.

If you can’t hear the clip, click here.

Being domain experts and having done one startup together gave the Caldon brothers confidence about starting Ballstar:

Vaughn: The confidence that we can start anything together , came from the fact that we had been the CEO and Director of Development of an organization that we created, and we started interacting on that level. …

The next step (in confidence) was knowing the space. We’re from Brooklyn, we play basketball, we know basketball players. …

… people got on Twitter because Shaquille O’Neal was there first … (Keeping that in mind) we … led with … aspirational leagues.

We went to sign up leagues like West Fourth Street, EVC at the Rucker, Dykeman, Tri-State Classic. These are all iconic leagues that people want to be involved and want to be affiliated with, so getting them on the platform first and catering to them, building that as our customer, and developing those customers was our focus. We knew we could do that.

If you can’t hear the clip, click here.

Here’s how they knew their idea could be a business

Nigel: It obviously started out as an absolute passion (for us).

We had to back-end our way into, figuring out, where is the business (model) in that? You could sell ads or you could sell the data. What we really found that our client was essentially the basketball league, and we could throw ourselves in the middle of the transaction.

There’s almost $2 billion spent in North America on paying to play basketball. If I’m providing a platform-as-a-service to amateur basketball leagues all over the world, now I have the opportunity to take a transaction commission the way Uber does. You can download Uber for free, but as soon as you hail a cab, you’re paying. Download BallStar for free, as soon as you want to play basketball, leave us some change.

If you can’t hear the clip, click here.

Customer discovery paid off for Kerry

Kerry: I listened and it was magic. Everyone started raising their hand and saying, “I have this problem, I have that problem.”

Steve:  Did you know you were doing customer discovery?

Kerry: I did. That was a key to my consulting business. … The beautiful thing is when you ask the customers, they’re in the space, they understand it, and they also then have buy in, right, because you’re going to solve their problem … 

Steve:  For our listeners, this is a brilliant insight. It sounds like you practiced it perfectly. They essentially taught you what the product should do.

Kerry: Right. I have 13 products today and everybody says, “How did you think of those?” I say, “I never thought of those, I was just a really good listener.”

If you can’t hear the clip, click here.

Being self-taught, she said, gave her an edge:

I didn’t go to college. I just started working for people … in all kinds of different jobs. …. I was always really good at whatever I did, because I loved working so much, it was my passion. I’d always start getting promoted to another level, but I have this inner thing inside of me that I can’t describe, that as soon as I started to get promoted to management levels I would quit.

I would say, “No, I have a destiny to do something else, and I’m trying to find my way.” I always also struggled with this part that had to get back into help. I was always then also giving to charities, or working for charities, or working for churches, or youth groups. It was kind of this back and forth. It was this incredible path that people look back on and say that’s crazy.  

At the same time it gave me key foundational things that I look on today as a CEO I needed. … (Things) like accounting. I was a bookkeeper, and I managed properties for a long time. It taught me all the accounting principles. It taught me how to handle some of the basic general ledger things.

If you look at different steps in my path, and I’m like, “Wow, that was great,” because now as a CEO I know all these different tools that I needed. Traditionally, you might get that in college, but I didn’t go the college route, so there’s a lot of skills that I picked up along the way that enabled me to be who I am today as a CEO.

If you can’t hear the clip, click here.

Here’s the biggest thing Kerry’s learned from doing a startup:

Kerry: If you have passion and if you’re dedicated to this. It doesn’t matter who you are, where you came from, or what your education is. You can do anything. Everything is possible.

If you can’t hear the clip, click here.

Listen to my full interviews with Nigel and Vaughn and with Kerry by downloading them from SoundCloud here and here. (And download any of the past shows here.)

Next on Entrepreneurs are EverywhereJavier Saade, former associate administrator for the U.S. Small Business Administration, and Hillary Hartley, deputy executive director of 18F.

Tune in Thursday at 1 pm PT, 4 pm ET on Sirius XM Channel 111. 

Want to be a guest on the show?  Entrepreneurship stretches from Main Street to Silicon Valley, from startups to big companies. Send an email to terri@kandsranch.com describing your entrepreneurial journey.

One Response

  1. I’m honestly just amazed they faced so much adversity for their idea. I guess I don’t really know anything about being a pilot but it seems like a great idea to me! Who wouldn’t want a tablet instead of a hundred different manuals? I guess people just have a tendency to remain stuck in their ways…

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