Flipping the Script: Scott Kitun of Technori on Chicago Tech, Startup Culture, and the Evolution of Crowdfunding

3Points Communications
8 min readAug 27, 2020

Like many things, our “Flipping the Script” series was put on pause earlier this year as we attempted to navigate a business environment unlike any we had ever seen. But we have not stopped having conversations with our new media contacts, who are not only adapting to our new reality themselves, but by the nature of their jobs are exploring the stories and trends of many others throughout the pandemic.

With that in mind, the return of our Flipping the Script series features Scott Kitun, CEO of Technori. 3Points CEO Drew Mauck spoke with Scott recently over Google Hangout, discussing the Chicago tech scene, startup culture, and more. Read highlights from their conversation, lightly edited for clarity, below.

Thanks for talking with us, Scott. Most importantly, how have you, your family, and your business associates held up these past few months?

My family is good, thank you. My daughter turned one in June. I got to spend a lot of time with her that I wasn’t expecting to have. My wife is going back to school, although I’m not sure what the deal is with “back to school” as of now.

In some ways, I have really enjoyed quarantine from a personal and business standpoint. Very rarely in life do you have opportunities to hit the pause button. I’m not having to spend 3 hours a day in a car every day commuting into the city, and I have taken advantage of not wasting that time. I can run the business remotely and I don’t have to miss anything family-wise.

My team has taken advantage of the remote environment as well. Sam (Fiske, Technori’s Chief of Staff & Executive Producer) took a 25-day road trip to San Diego. My marketing manager moved in with her fiance in Madison. And we haven’t missed a beat.

Most folks in Chicago tech are familiar with Technori, but for those that are not familiar, please tell us about what you do and why you do it.

Technori has evolved quite a bit. We had “Technori Pitch,” our event showcase, which was selling out auditoriums. But I felt, as a community, we evolved enough and there were so many options to learn about these companies, it felt like we were becoming obsolete even as we were selling out events.

I started looking into building an equity investment crowdsource platform and in the process became an investor in Republic — where everyone there could invest. That was a huge win because it got everyone involved. We actually ran out of local companies to list, so Republic started flying people into Chicago and doing events in other cities.

We had enough traction that in 2017 WGN reached out and wanted to do a radio show. We said, we can do you one better: we’ll be the first ever show where an audience could invest directly into the company pitching. We did that and it worked really well.

We finished up the WGN show in July of this year and decided it was time to really lean into social media podcasts, as that’s where the majority of our audience is. Technori has evolved into a platform for individuals — any individual — to invest in private companies. It’s the evolution of equity crowdfunding — co-investing. Our audience gets to invest in the same round, and with the same terms, as the big players. That’s what excites us.

How have you evolved as an interviewer since your work as host was not something you aspired to be coming out of college?

I went back and listened to my first interview for shits and giggles — it was terrible.

I got the opportunity to do a WGN podcast because I had worked with them before. I had never hosted shows before I went to Medill, but they probably thought, “he went to media school, he must be good.” I literally wrote every single thing I was going to say. The headline, intro, questions — even things like, “you will say this if they respond this way.” It was basically propaganda.

Like anything else, you get 1000 interviews under your belt, you start to get cues, you start to get comfortable. You learn why your guests are coming on — they want free press. I’m interested in the story. I need to figure out how to dissect what you just said in layman’s terms.

I learned how to be conversational, get the guests to relate to me in some way, break down what they do, and utilize what I’ve learned in the thousands of interviews I’ve done beforehand. It’s really an art.

Speaking of which, glorification of early stage companies and their founders can lead to incorrect estimations of what is required to launch a successful technology company — do you ever think that we as communicators in this Chicago tech space go too far with our adulation?

I think we do almost all the time. There is a selfish desire to think that the city is full of unicorns. I get it. I’m talking with World Business Chicago about how to bring business to Chicago. For Technori, it’s in my best interests for you to think we had companies that raised $1M-plus — the more the better.

The more we say “this is the next Uber,” for example, more people are going to click on it, which means more ad dollars. We are all guilty of making people bigger than they are. Just like anything — child stars, athletes — these founders get famous, they get a big head, forget where they came from, and they become divorced from the real world.

But at the same time, I’ve never seen a city sell itself as “we’re average.” You have to promote yourself. So it’s a balance.

When should a startup stop using the term “startup” to describe itself?

A startup is an idea and an unproven hypothesis that there is a scalable and profitable business behind the idea. Once you have proven the pillars of a startup as true or untrue, then you graduate to a business that you try to scale.

To me, you are a startup until you either scale or you fail. I have pissed off a lot of founders who got mad because I called their “company” a “project.” Your project could work under certain circumstances, but you need all this money to determine if it will work or not. You’re not a company until you have determined that and are making money.

How will the pandemic, and more specifically the majority of the tech workforce going remote, affect the cities that traditionally have represented tech excellence and entrepreneurship?

From a real estate perspective, I’m very scared. Companies were buying big expensive offices downtown, making them fancy, etc… But now people have started to realize, remote working is a different lifestyle, and maybe it’s better. Businesses used to say “there’s no way we can have a 2–3 day week in the office” — now it’s something everyone is considering. Locally, we’ve seen Snapsheet and others putting their places up for sublease.

Cities are going to have to spend money and resources to give breaks to make these companies want office space there. And, the big picture is not about COVID, it’s about the bottom line. Where do you live, what do I have to pay you? You can live in Davenport and work for Facebook, and that’s a lot cheaper than living near the headquarters in the Bay Area.

If I’m a young person though, I want to live in a place that’s a lot of fun. So if I’m a company, I will still want to set up shop in these fun cities, because that’s where young people want to party. I will set up a presence, I will train them up, pay them, and once they hit a certain level, I will tell them they can live wherever they want.

So office spaces will come back in cities like Chicago, you just won’t see five floors of people from the same company working together anymore. They will come back differently, and smaller, but you can’t just pull out of the area and away from all the graduates who are living or want to live there.

What are a few cool pivots you’ve seen from Chicago tech companies that were made because of COVID-19?

  • PartySlate — they’re leaning into and embracing the future of digital events. Their pivot to connecting people online ensures that companies are staying engaged and are productive.
  • Rheaply — they are a circular economy company that set up a PPE Market with the City of Chicago. [NOTE: Rheaply is a 3Points client.]
  • Keeper Security — they have been booming already, but they will be booming even more. Remote workers need to take their laptops out of the office, which increases the chances of security breaches. During any time of crisis or chaos, that is the most likely time to get hacked — everyone is very vulnerable. Keeper didn’t have to pivot, but the market pivoted for them.

Very importantly, who are a few people of color in Chicago’s tech ecosystem that more people should know about?

I’ll give you a few: Garry Cooper from Rheaply, who you already know; Stella Ashaolu from WeSolv and Shaniqua Davis from Noirefy, both of whom are focused not only on bringing more diversity to the office-place, but improving workplace culture so that people of diverse backgrounds will better fit in and have a far greater chance to successfully advance their careers; and Jasmine Shells from Five to Nine is just a force to reckon with. It’s one thing to host events and team meet-ups, virtual and in-person, but it’s entirely another to track and analyze these actions so we know that we’re not just quota matching.

In their own way each of these founders are building a better future, rather than just talking about a better future.

What’s next for Technori?

Command and conquer — we want to democratize entrepreneurship, allowing founders to pitch their business to anyone, no matter their background. How can an investor who is not rich participate? I want people of all backgrounds to pitch and people of all backgrounds to be able to invest. We want to make these opportunities available to everyone. That’s why we have moved our medium from stage to digital to social, and we will continue to move to wherever the people are.

Thank you to Scott for taking the time to talk with us. He is a great promoter of our talent and we appreciate all the work he has put into helping Chicago’s tech ecosystem improve and expand. If you’d like to learn more about the work we do with media outlets like Technori, please reach out to info@3ptscomm.com.