Episode 26 - Robert Blacklidge Interview

courseAlign.io, StartupBus and Local Entrepreneurs. Music from Carlos Strong


Show Notes

On this episode I interview Robert Blacklidge who is very active in the local Tampa Bay startup and entrepreneur community.

Also featuring music from a great local musician and producer names Carlos Strong!  We’ll be having more music coming in the future from Carlos, he’s that good!

Transcript at the bottom of this page!

Robert Blacklidge

On this episode I interview Robert Blacklidge who is very active in the local Tampa Bay startup and entrepreneur community.

Startup Bus


One Million Cups

Twizzzzzzz the night before candy

Hershey’s produces over 1,000,000 miles of Twizzler rope every year.


Kyle Sasser is a Tampa Bay Native as well as a local Realtor.  If you’re looking to find your own great place in Tampa Bay I’d love to help!

Great Things Tampa Bay is hosted and produced by Kyle Sasser.

There was no paid advertising in this episode.  All recommendations are given based on personal experiences.

Also featuring bumper music by Author:Oscar Woods Title:”Dont Sell It Dont Give It Away”.


Robert: In 2015, I had just lost a half a million dollar business. And I went home, looked at a red Fiat 500. Despair and misery and distraught, I ripped the seats out of it.

Kyle: Okay.

Robert: I’ve put a bed in there and a dresser and some fans, and I hit the road. And with no real destination, I just started heading northeast.

Kyle: Hey, everybody. This is Kyle Sasser. This is Great Things Tampa Bay. And today, we have a interview with Robert Blacklidge. And he is very active in the local entrepreneur and Veterans Community. So, he’s very high-energy guy, a whole lot of fun. And probably gonna be spending a week with him on the StartupBus which is a school thing. Anyway, I don’t wanna run the whole interview. Give it a listen and I hope you like it.

Hey, everybody. Kyle Sasser here and this is the Great Things Tampa Bay Podcast. I’m here with Robert Blacklidge. He’s the founder and the CEO of Course Align. Also, heavily involved in the Tampa Bay startup in entrepreneur community. He’s also the current floor to StartUpBus Conductor, part of Veterans of Florida, organizer of BizPrints, and also has a very dashing beard.

Robert: Thank you.

Kyle: If you like to say hello there, Robert.

Robert: Hello. There we go.

Kyle: So we’re getting together today because you’re very active in the startup and entrepreneur community. Just kinda wanna give us a brief overview of what got you started in that?

Robert: Well, it’s a really interesting story. In 2015, I have just lost a half a million dollar business. And I went home, looked at a red Fiat 500.

Kyle: Nice car.

Robert: Oh, yeah. I actually really enjoy the car. But I was lost. I didn’t know what to do. And so, really, out of…I don’t even know how to explain it but, you know, despair and misery and distraught, I ripped the seats out of it.

Kyle: Okay.

Robert: I’ve put a bed in there and a dresser and some fans, and I hit the road. And with no real destination, I just started heading northeast. And I drove and drove as far as I could until I hit this town called “Lubec.” It’s the most eastern city in the United States. And there was a ferry. I was like, “Okay, I’m gonna get on this ferry.” And I hop on the ferry, and it actually took me up into Canada. And in Canada, there’s roads of blacktop that just stretch as far as the eye can see. Spruce trees that reach through the sky and mountain ranges that go on forever.

And there, I just drove forever, what felt like forever, until the road turned into dirt. And I drove until the road ended where I got out of my car, put my hands on the door and stared up into a mountain that reached through the sky. And standing there, I thought to myself, I’m like, “I did not just drive all this way to get stopped by a mountain.” And so I grabbed my bag and I put it on my back. And I started up that mountain, one hand over the other, reaching up and climbed up that mountain through trails that were overgrown with trees that barely had enough room for me to go through this path that’s kind of like “The Secret Garden,” if you’ve ever seen that. Pushing my way through and out the other side, I came out.

And there was ocean that just stretched forever with waves crashing on a marbled stone coastline with grass that’s stretched out with this little coast there. And there were some ruins. And it was very overcast. And I really didn’t know what to think. It was beautiful, but it was sad. So I stayed there for a little bit, and, eventually, turned around and headed back up the mountain. And when I came over the top, it was the most beautiful sight I’d ever seen. The sky was on fire. The ocean outstretched just lit with the sunset mountain ranges that reached forever. And I had this epiphany and a realization that in my life I had chased money. And I have lost everything in a moment, and then left with nothing but the ruins like the ruins on the beach behind me.

And in life, you can pursue money and be left with nothing or you could pursue passion. And in that moment, I decided to pursue my passion. And my passions are entrepreneurship and education. And since then, I have lost more businesses than I had ever had before. But each one was a progression on the last, and a personal growth in the relationships that I gained have really grown me as a person. And I will not regret that. And I encourage others now to pursue their passions in life.

Kyle: It’s true. You definitely…you cannot be afraid of a failure because, you know…like, you honestly…you never really know whenever you’re starting something if it’s gonna be a success or a failure. So, you just kinda have to go into it, you know, fully expecting that maybe it’s gonna fail but you’re gonna learn something along the way and then apply that on the next venture.

Robert: It’s something interesting about passion. And I live by an ethos now of persistent passion and intentional serendipity where it’s kinda like caring about sports. You can care about your sports team. You can even be persistent with it and we watch them every Sunday. But the really amazing thing doesn’t happen until you start putting that intent in the world where you Tweet at this football player or this sport team player. You go to the games. And then serendipity, the world comes back and you meet the players or you go to the dugout and they’re really amazing things because the world responds when you put that intent and you are persistent with your passion.

Kyle: It’s very true. It’s very true. So you went into the wilderness.

Robert: I did.

Kyle: Shall we say a walkabout almost?

Robert: You know, I think we’re lost. We…I think our ancestors knew something when they sent our youth into the wild.

Kyle: And just personally, my niece is currently on sort of one. She did the same thing. Tore the backseats out of a car and then made it all the way up to Alaska about the same year, honestly. So…and she’s still, you know, touring around out West and stuff, you know, figuring out what she wants to do. So, of course, you know, that upsets the parents and all that. But, whatever. It’s like, “Yeah, they’ll be fine.” They’ll figure it out just like the adults figured it out.

Robert: I think the big takeaway for me was that you have to find that thing that keeps smacking you in the face, that passion. And then water it, right? Your passion…a lot of people see the end results, right? They see the forest but no one sees the seeds that were laid…

Kyle: An overnight success that took, you know, eight years in the making.

Robert: Correct. And so, what’s important is to be persistent and water that seed over time. And then when it’s a sapling, then you plant it in the forest and let it grow and then the world starts raining on it and growing that tree.

Kyle: Like, my personal mantra that I use for the Podcast or business or…is “No zero days.” Like, every day, whatever my goal is, I make sure that I, at least, make some incremental step towards it.

Robert: You know, it doesn’t have to be big. It can be so minute. But that one little push that go into that meeting, go in…to be where I am today, the amount of astronomical odds that had to have happened to occur to get me to where I am, I bless my…I count my blessings all the time. It’s really incredible.

Kyle: The only way to guarantee a failure is to never start in the first place.

Robert: Absolutely.

Kyle: So you found your passion, and what was the next step on your journey after that?

Robert: So, I actually spent two years growing my passion, going after the education system. So I graduated with an MBA and thought, “I could then go get a job, right?” So I looked at job board after job board that had entry-level jobs. And I found something really interesting. They required experience. How do you have an entry-level job requiring one to two years’ experience? So I started a company to solve this problem. If the problem’s experience, I’ll hire people right out of these programs, train them, and then we can give them the experience they need so they can then get the job.

But what I discovered was they didn’t even have the skills to do the job. So, from there, I shut that down, started teaching, and realized that teaching was just going to be too slow. I developed a course in Python for Data Science but it was 7 people, 12 weeks of training, and it wasn’t very scalable. So while I was developing that process, thinking about how to grow that, how to develop that, I ended up moving to Tampa. I was working at a second Master’s at the time. I actually was supposed to come to Tampa and just sit at the pool and do my homework. And, you know, I have this entrepreneurial mindset. I had several companies and sitting by the pool only lasted about two weeks.

I ended up going to 1 Million Cups which is an incredible pulse on the community, really shows you what’s going on in the entrepreneurship community. And I went to the one here locally in Ybor at the Entrepreneur Collaborative Center. And this is where serendipity comes into play. Just so it happened that operation startup, a local veteran entrepreneur effort happened to be pitching that day. I’m a veteran. I’m an entrepreneur. I was like, “How can I get involved?” They’re, “Great. Come be an entrepreneur and a resident.”

I have this uncanny ability to see the landscape and identify the gaps and how we can fill them. So I saw all these great resources that help veterans get their ideas up off the ground, give them a good foundation, get a few customers, get started. But then they have a gap or a wall that they’ve hit and didn’t know how to get over. So, being brand new to Tampa, I started an annual event. It was really amazing. I had over 100 community members come together, fund an event that moved 10 veteran entrepreneur businesses forward. And that really inspired me. It showed me the community that was here in Tampa that supported the entrepreneurs and really inspired me to pursue my own ideas and pursue being involved in the entrepreneurship community here in the Tampa Bay area.

And then I heard about this really incredible thing called Startup Bus. And having this idea about the education system and having tried a couple different ways to address the issues that I was having with my education which actually was really phenomenal, I never really saw any value in my undergraduate. But my graduate program was practical application of theory. And I have received tremendous value of it and could not understand why I wasn’t able to get a role in the organization doing it until I went and saw the problem firsthand is that it got reaction that from the fact that these employers were seeing people exiting education systems without the skills they needed to do the jobs, you know.

And now I know that 89% of the employers feel that graduates do not have the skills to fill the openings that they have. So I went on the Bus and it was the purest, most organic entrepreneur experience I ever been on. Literally, it’s the combination of a hackathon and a startup weekend. And if you don’t know what those are, those are essentially a group of people…a startup weekend, it’s a group of people in a room, an auditorium, typically, and they’re typically strangers. One at a time, they have an idea. They pitch it to the group and if people like it, they work with them over the 24, 48-hour period to get as much traction on the idea and then pitch it back to the group.

Well, someone thought it would be a cool idea to do that on a bus while it travels across the country and then pitch in a destination city rather a bunch of other buses all across North America doing the same thing. So my bus, last year, we had seven other buses, so eight altogether, traveling across North America, headed towards New Orleans where we pitched against each other.

Kyle: And you could hear this process…

Robert: You can.

Kyle: Because there was…it was on Gimlet Media, right?

Robert: It was Gimlet Media, did a five-part series on their startup Podcast for StartupBus. It was really incredible and it truly captures the experience. Really phenomenal. This year, we’re doing it again, April 27th.

Kyle: My birthday.

Robert: Through May 1st. You’re gonna be on the bus with us. I’m just super excited.

Kyle: I’m tagging along on this experience.

Robert: I’ll be conducting. I’m the lead conductor which is a really humbling experience for me to be able to give back in that way and really help a whole another generation of bustrepreneurs through that experience.

Kyle: And there’s how many people on the bus usually?

Robert: It’ll be 30.

Kyle: So 30 people take space, three days, very heated and emotional, you know, because you’re talking about people’s babies and, you know, they’re tied to their ideas and…

Robert: I like to think about it as a once in a lifetime opportunity to fail without consequence, right? It’s caffeine-fueled, lack of sleep, high-intensity. But we take you across the country. We provide you with guidance and mentorship. And we stop at some of the world’s…the country’s natural wonders and cultural hotspots. So this year, we’re looking at stopping in Atlanta which has an incredible tech hub, Nashville which has some incredible cultural hotspots, and really bringing in that community that exist in the tech environment and exposing you to more than really what you see in most of your life. And you get hyper-connected into that community as you travel across the country.

Kyle: And on the Gimlet shows, they followed the New York bus and they would stop and kinda, like, give pitches along the way to kinda refine their ideas to, like, local business owners and people in the community, right?

Robert: Absolutely.

Kyle: And they would give them honest and sometimes, you know, harsh feedback that, you know, the idea needs to be refined further which is invaluable because a lot of times you get tied onto this idea. And, you know, it’s not going to work or it’s too broad. You need to narrow it down and…

Robert: So a lot of these individuals that are on the bus aren’t entrepreneurs. They’re your co-worker. They’re your designer. They’re your first-time developer right out at school. They’re, oddly enough, the retired executive who has been working for years looking to explore something new. And it really gives them the opportunity to work collaboratively with a diverse group of individuals and be exposed to a lot of different point of views. It’s really eye-opening and really amazing to get that exposure to have to work hard and fail fast.

And, again, in life, you don’t get those opportunities to fail and then pick up and then move again, and then fail, and then pick up, and then move again. And this gives you an opportunity. Essentially, it’s the first year of a startup in one week, you know. We call it “The Bootcamp MBA.” It’s like the Navy Seal’s training. It is that intense. Your personal growth on that experience and on that road trip is like no other.

Kyle: And I’ll be documenting the process and I’ll probably be doing like a series, I would imagine, just, you know, similar to Gimlet’s but focused on the Tampa group.

Robert: That’s in Florida. So we actually…I already have people coming from Atlanta. It’s really the southeast. And so…

Kyle: Okay, the southeast. But I’m gonna call it the Tampa bus.

Robert: Orlando, Miami, all across the region. It’s gonna be really phenomenal. We’re gonna be meeting with the buses from New York and Saint Louis and across the region as well. And then we’ll end up in New Orleans during Collision Con which is really cool. We have some cross-pollinations. Some of the judges will be…some of the speakers from Collision Con.

Kyle: Awesome. That’s awesome.

Robert: So it’s really really cool. The whole power of this is, at the end of the day, the people you meet. And we bring in a lot of the tech community and really get you some friends. I mean, I have friends all across the country from all different sectors of life. And it’s really really incredible.

Kyle: So you have the…so you found the passion and then you had your idea. And then you took that idea on the Startup Bus. So where is that idea now?

Robert: So Course Align has really evolved into a amazing company. We use artificial intelligence on the job market so that educators can align their curriculum to meet employer demand. Essentially, what we found is that 89% of employers feel that educators don’t have the…89%…let’s cut that. What we found was that 89% of employers feel that graduates do not have the skills they need to meet employer demand.

So we looked at the education system, talked to Deans, talked to professors and tried to find out why this was happening. And what we found was the way they develop curriculum was extremely manual. They literally go out and talk to employers, come back and discuss what that means and how to develop the curriculum. It can take two plus years to analyze a market.

Kyle: And it almost sounds like sort of like the old trades…you know, the trade schools, you know. If you have…like the shipyards here, if they notice that the graduates aren’t able to do certain types of welds, a lot of times, you know, they’ll go to the trade schools or the Union or whatever, will be like, “Hey, this is what we need. Please focus on that.” But, yes, it’s a very…

Robert: Extremely manual process which worked when you had 40 employees and a few thousand jobs. But when you have 4,000 employees plus and 40,000 plus openings, you can’t find out the aggregate of those job needs. So by using modern technology, we aggregate all those employers’ needs. And then we identify those needs to the universities. And then we also take in a step beyond that, and we actually analyze and we look at what the university is teaching.

And that does some really really powerful things. We can identify where the mismatch is so they can make immediate adjustments. It identifies the parts of the curriculum that do not need to change because, at a whole, they don’t change over time. And we can provide them the ability to stay in tune with their accreditation. Now, this is important because over 50% of their funding comes from State and Federal sources. And then the recent years, over 30 states in the United States have passed laws, Florida included, that require them to align their curriculum to the market need or lose their operating budget.

Kyle: Okay.

Robert: That’s huge. And in response, they’re spending a billion dollars nationally on market assessment. And they still [inaudible 00:21:52] because they’re using manual processes to do it.

Kyle: Definitely the old…you know, it worked back in the day so let’s just keep doing it so.

Robert: It’s…you know, it’s the monkey and the banana with the hose story.

Kyle: And honestly, it’s not…a general education will really only get you so far. Like, most career paths are so specialized nowadays, you know, for like… Just on the IT side that I could think of, you know, you have network engineers, database administrators, data warehousing and analytics and all…you know, all of these very particular things. And it’s all under the IT umbrella but tremendously different skillsets…

Robert: It is.

Kyle: To be successful at each of those.

Robert: We have no desire to really tell them how to develop curriculum. Our goal is to give them better information so that when they develop curriculum and as they develop curriculum, they’re more in tune with the market need. In my mind though, I see that they’d be able to identify the pieces of the market that don’t change over time, right, because when you look at Computer Science, the core of it is ones and zeros. We still need to teach the ones and zeros. But those specific curriculum pieces that are attuned to the database management, right, the tools change. So that last semester, the Capstone projects, they need to be tied directly to the jobs that the students are applying for today.

And the problem is if it takes two years to find out what those employers need, how are you ever gonna make a capstone that meets that needs?

Kyle: Especially in tech because they move so fast.

Robert: Course Align tells them today what that job is and what they’re hiring for. So as part of being in a startup in the Tampa Bay area, it is giving me an incredible opportunity to really engage the startup community and really be a part of the Tampa Bay entrepreneur community. I have had the opportunity to help organize the Startup Week, the Biz Print which is a veteran-focused event. We’re going to be participating in Synapse Florida which is a huge aggregate of essentially national entrepreneurial efforts, local entrepreneurial efforts. Its connection between everything that’s going on in the Tampa Bay area. So I highly recommend you attend that.

What’s really really impressive is that Tampa Bay is starting to recognize that there are all these really incredible events in the Tampa Bay area and that entrepreneurs or people that are interested in entrepreneurship or wanna be involved in it are coming and engaging in these different pieces, the Tampa Bay Wave, Operation Startup, Startup Week. And they don’t know where to go next. So we’re starting to create the bridges that connect you and guide you into the next piece.

If you’re at this stage in your entrepreneurship journey, this is probably where you wanna head next. This is how you get to here. This is where you head. And so those resources are starting to come online, starting to help you bridge those gaps, starting to help you connect it.

Kyle: Let’s start here. So if you were…didn’t know anything or anybody, what would be your first step into entrepreneurship to take advantage of the tools that you now know about? What would be your first step if you were starting from zero?

Robert: So I really like 1 Million Cups. So 1 Million Cups is an event that I go to every Wednesday morning. And that is the heart of the entrepreneurship community. The networking that happens there changes every week. That’s what’s powerful about that event. Every week, there’s a different group of people that go there. There’s a core group that tends to show up every week, but there’s a percentage that changes out regularly. And then that ties you into that network of resources that are there.

The one in Ybora is at the Entrepreneur Collaborative Center which is a county resource that has all sorts of events throughout the week that you can gain information on how to get started, do social media, all sorts of different pieces of the puzzle that you can get access to. From there, there’s events like Startup Weekends, Hackathons. Startup Week is once a year. They’re an organization that will be hosting events throughout the year as well. The Synapse is a major event that’s coming. That’s coming up on the 28th and the 29th.

And then just keep on paying attention to different events. There’s Hillsborough Homebrew that happens once a month at the end of the month.

Kyle: Okay. And we’re gonna have links to all this in the show notes. So…

Robert: Absolutely.

Kyle: So that people can connect with this. If someone wants to connect with you, what’s the best way to do so?

Robert: You search my name. I’m on LinkedIn, Instagram, all of the major social media accounts. You could definitely connect with me. I have over almost 8,000 LinkedIn connections.

Kyle: Nice.

Robert: So you can definitely leverage that.

Kyle: Course Align’s website is…

Robert: Coursealign.io.

Kyle: All right. And was there anything that you wanted me to ask that I forgot or didn’t ask?

Robert: I think we covered everything. I think the most important thing is that to be persistent in your passion and then put that intent into the world, and serendipity will happen.

Kyle: I believe it. Well, thank you so much for being on the show.

Robert: Pleasure. Absolutely.

Kyle: And check out the show notes. We’re gonna have links to all of the resources that we’ve talked about. And if you’ve been kicking that idea around, it’ll probably be a little bit too late to get on this StartupBus.

Robert: No, yeah.

Kyle: Well, this is gonna come out, like, a week or two so it might probably…

Robert: No. You can get on the bus morning up.

Kyle: Okay. So, the bus is…you know, my birthday, April 27th, 2018. So, put your applications in.

Robert: Get on that bus. Jump on there.

Kyle: And if you just have a idea, like, don’t wait around. Just start taking baby steps towards them.

Robert: Absolutely. Every little step that you take towards it, you will be amazed at how much the world responds.

Kyle: Yup. It’s good stuff. Thanks so much, Robert.

Robert: It’s always a pleasure.

Kyle: All right. And now, here is your fact. Hershey’s makes over 1,000,000 miles of Twizzlers every year. And definitely, you know, the red licorice versus the black licorice, I gotta go with the black, I’m sorry.

So I hope you enjoyed the interview. And, in fact, we’re gonna play out today with a music from Carlos Strong. He’s a music producer and doing some amazing work. He’s based out at Tampa. So this track is called “Heartbreak.” But before we get to that, just want to let you know a couple of things. One, if you’re looking for your own great place in Tampa Bay, I am also a local realtor in addition to being a 40-year native. And I would love to work with you and help you find or sell your home here in Tampa Bay.

So you could reach out to me at my email which is kyle, K-Y-L-E, @greatthingstb.com. That’s G-R-E-A-T T-H-I-N-G-S-T-B.com. Also, if you enjoyed the Podcast, it does cost me a couple hundred bucks a month just for the editing and hosting and all that good stuff. So, if you’d like to help out, just go to the website greatthingstb.com and there’s Amazon link there. Just click on that and shop on Amazon as you would normally. And throw us a couple bucks to my account to help offset the cost of editing and hosting this.

I’d like to thank you for tuning in. I’d like to ask you to share this with one or two of your best friends. Show them how to listen to a Podcast, how to subscribe, and to keep up to date. And, I’d also like for you all just to stop by the website. And we have some forms there. We’re talking about local things, and, you know, we have places to eat and things to do. All sorts of good information. So that’s…the website again is greatthingstb.com.

So, once again, this is Carlos Strong. And the name of this track is “Heartbreak.”

I’ve taken all the pain that a man can take.
Now, my mind is spinning.
My heart is heavy.
Just let me run away from all the hurt that I’ve been to.
While giving love you wasn’t giving me,
I never really understood.

‘Cause I tried to make it work but it ain’t worth it.
So I gotta leave before it gets too late.

‘Cause I can’t take another heartbreak. I can’t take another heartbreak.
I can’t take another heartbreak from you.
I can’t take another heartbreak. I can’t take another heartbreak.
I can’t take another heartbreak from you. So we’re through.

I say that the last time will be the last time you break my heart.
Though loving you was easy but you didn’t have to take it this far.
I gave you everything, everything I had to give.
This time, I’m leaving. Never to return again.

‘Cause I tried to make it work but it ain’t worth it. No.
So I gotta leave before it gets too late.

‘Cause I can’t take another heartbreak. I can’t take another heartbreak.
I can’t take another heartbreak from you.
I can’t take another heartbreak. I can’t take another heartbreak.
I can’t take another heartbreak from you.

Sitting here thinking about the way things used to be. And how I gave you all my love.
You took for granted all the love and time I’ve given you.
Said, I’m done. This is it. I’m tired of all your bull****.
And I just can take it no more.

Take another heartbreak. Take another heartbreak.

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