From the Ground Up: An Interview with Dan Olson of UpCity

Q: The team has been planning on having you sit down for one of these From the Ground Up interviews for awhile now, Dan. With our recent rebrand, I thought now was as good a time as ever to bring you in!

A: It’s great timing! We’ve been around for quite awhile, and we’ve gone through a number of different iterations. I’ve loved hearing our partners’ stories, but it’s also good to refresh our partners on our history; we have some of it on our site, but it’s nice to be able to share our own entrepreneurial journey – which has been exhilarating, to say the least.

Q: Couldn’t agree more. So, let’s start from the beginning: tell us about how UpCity came to be.

A: I’ve been in the startups and digital marketing space for a long time now. It all started way back in 2000 when I was first getting into startups and I was fortunate to come across a company that was really early in digital marketing, Performics. 

At that time, there was no Google, there was definitely no Facebook, there really weren’t any of today’s Internet giants. There was AOL and the beginnings of display, but it was all very first-gen. Media was fragmenting; well-established models that were based on a YellowPages-style industry (think: delivering paper to the front door) were in for a rude awakening. Being part of the early stages of that was pretty amazing. We started to see this thing called Google grow and were actually able to help beta test it; at Performics, we were some of the first few people on the Google platform. They had three people in their Chicago office and now they’re trying to hit the 10,000 person mark. It’s crazy to see.

Q: That must have been pretty insane. What was that like?

A: We worked almost exclusively with enterprise-level clients like HP, Target, and Kohls. I was about the 20th employee, so I was in on the ground floor when things were really small, still fresh. We had some venture capital and had the opportunity to just try to make a go of it. It was a great culture with a lot of smart people and I ended up learning just as much from the people I worked with as from the people I worked for. That kind of dynamic culture where everyone is a stakeholder provided a great blueprint for the type of culture that I wanted to build whenever I started my own company.

It was a great culture with a lot of smart people and I ended up learning just as much from the people I worked with as from the people I worked for. That kind of dynamic culture where everyone is a stakeholder provided a great blueprint for the type of culture that I wanted to build whenever I started my own company.

Fast forward a bit and we were starting to take clients from established firms like Starcom and Leo Burnett. It was a new industry and we were growing along with Google; we offered affiliate marketing, paid search, and I actually got to incubate our search team. There were a lot of growth pains in that process too and a lot of times, when I was young, when it was easy to look at the situation and think that people just need to suck it up and try harder. Luckily, with that team it was so dynamic and it was great to have my eyes opened to the fact that as we scaled, our technology stack started to deteriorate, we didn’t have an HR function so people were pulling double duty, there wasn’t a fixed hiring process. Things like that can really put a stop to a great business, but my time at Performics really let me think about what that a growth playbook looks like, what those pain points are, and what types of solutions can be implemented.

Q: So what made you shift from that enterprise world into more local businesses?

A: Towards the end, I was getting excited about helping small and medium-sized businesses. We were helping companies like HP who could spend six or seven figures to hire the people and technology to figure this stuff out for them. What were the small business owners supposed to do in this new digital world? 

Eventually, Performics was bought by DoubleClick (which was itself eventually bought by Google) and as part of that process the group I had built got spun off to Publicis. There were no product people or developers around this anymore, it was just the service side. My ideas about small to medium-sized businesses that I had been bringing up in strategic planning sessions for years weren’t going anywhere, so I thought it was time for something new.

Companies like Groupon were beginning to take off at the time so there was a lot of movement in the SMB space. I was fortunate enough to connect with two other gentlemen, Patrick Gavin and Andy Hagans, who had a pretty interesting idea. They had talked to a lot of people who would ask them how to optimize their sites, so they looked at companies like MailChimp and to see how they brought email marketing to the small business owner. They wanted to do exactly that, but for SEO.

We knew it was going to be tough, but we launched in April of 2010 as DIYSEO. Our mission really hasn’t changed since those first days: how can we help business owners evolve their marketing with the times. At that time, we created a DIY software to let business owners handle their own SEO. There was a lot of frustration, confusion, and tactics that worked and some that didn’t. Ultimately, our biggest takeaway from that was that it was getting more and more complicated to figure out things like SEO, social media, local, all these things, and from a tactical perspective, it was just overwhelming for business owners. They need help; they need providers who can come to them and help them get these things figured out, so we started thinking about the channel and agencies and marketing providers in general, and started to rework our software around that. That’s when we rebranded to become UpCity.

Our mission really hasn’t changed since those first days: how can we help business owners evolve their marketing with the times.

Q: I started here not too long after that rebrand if you recall!

A: Absolutely! I was one of the ones that interviewed you! As you know, we really wanted to create a brand that was about how we can raise the bar in the industry. There’s a lot of snake oil. We saw the confusion and frustration in the SMB side, which has gotten better but still exists today. That led us to partner with people we thought were doing great work out there and helped them leverage our software to service their clients. It was a great iteration for us and we learned a lot from those folks, but what we consistently heard from our partners is that they could use more leads…more traffic…more of those types of things.

That led us to our third iteration of the business: the Marketplace. At the beginning, we had a really basic free offering where we created a Yelp-like app for our partners to promote themselves. Our first list was web designers in Kansas City and surprisingly enough, it worked really well. SEO was in our DNA, so from the start we made sure that things were optimized. Our rankings started to pick up and we started to get inquiries from other marketing providers that wanted to be featured as well. 

Being a SaaS business, we already had a lot of data in our SEO software from our clients; we had a lot of internal systems built up that could supply us with a large quantity of data rather easily. We were already tracking things like rankings, domain authority, reviews, and other similar indicators of a company’s web presence, so we thought: what if we take all these metrics and apply them to everyone in our Marketplace? What we created was a really great algorithm around who someone is and how recommendable of a provider they are.

The next step was adding in our own first party reviews where we weren’t just looking for five stars. We actually wanted to dig in and find out about the experiences that customers were having with each provider. Those review efforts have really helped propel our recommendation engine and have allowed us to more accurately rank our lists.

And that brings us to today, where we’ve recently expanded our Marketplace to include not only marketing service providers, but B2B service providers of all kinds. That algorithm we use to define a great web designer can also be used to describe an IT services company or a business accountant. There’s just not enough structured data around some of these providers in the B2B space. When businesses are investing thousands of dollars in marketing, and they can find more information about “great places to eat in Chicago” than they can for the marketing agency they’re hiring. That’s a problem. I think that’s crazy. So coming full circle, we’re excited about getting more structured data, getting better data in general, to help buyers make much better business decisions than they ever have in the past. 

That brings us to today, where we’ve recently expanded our Marketplace to include not only marketing service providers, but B2B service providers of all kinds. That algorithm we use to define a great web designer can also be used to describe an IT services company or a business accountant.

Phew. How’s that for an answer?

Q: Definitely thorough! It’s clearly been a long journey over the last almost 20 years of growing this company. What stage would you say has been the most challenging for you? And what stage has been the most enjoyable?

A: I think the most challenging one was those early months when you’re just like, “Man, is this a business or not?” I think that product market fit stress is really challenging and it can be really hard to work through with people, especially when you’re pre-revenue. It’s also exciting because you’re in experimentation mode, you’re doing lots of different things to see what works, you know?

Q: Absolutely.

A: I’d be fine skipping that phase next time around if I were given the option! 

The other part that can be challenging is when you’re in a good spot, you’re doing great things, but you’re not seeing the improvements in your numbers. We pride ourselves on being very transparent and there are times when we’ve been at the same revenue number for awhile and it hasn’t been the most exciting growth story. That can be tough when everyone is working their butts off to make this thing successful, but I think you can agree that these last couple years have been an exciting time for us here with a lot of growth. I feel like we’ve really found the right business model and the right product market fit, so this last year when we’re growing at 100% year over year has just been awesome. I’d have to say that right now is the most enjoyable stage for me.

Q: Can’t argue with that! So, having been in the digital marketing industry since the very beginning, where do you see it all heading? What are your thoughts on the future of digital marketing?

A: I think structured data and better decision making are going to be huge. If there’s one thing that the Internet has done a good job of over the last 20 years, it’s helping people make better buying decisions. Sure, there are ways we are worse off than before the Internet (media fragmentation, fake news, whatever the case may be), but one thing you can be sure of is that you can go online and find more and better information about the products and services you care about than ever before.

There’s a lot of review data out there on products, and I think the B2B world is just catching up. Companies are just starting to realize what we’ve been preaching for awhile now. To be successful today, you have to not only have a really good offering, you also have to treat your customers exceptionally well. Then, you can leverage them and build a brand off your reputation. Word-of-mouth has been around for a long time, but you know, what’s old is new. 

To answer your question though, structured data will be huge.

Q: My final question for you is where you see UpCity fitting into this new landscape of structured data? 

A: Well, we’re knocking on the door with about 10,000 reviews and I believe we can set a roadmap to where we’ll hopefully be ramping up to 30,000 first-party reviews around B2B service providers of all types in the near future. That will be a huge push for us as we seek to help B2B consumers make better business decisions, but the other side of that is education.

We have to do a lot to educate our partners about building a reputable brand. We talk about the flywheel and there are a lot of companies that do that really well. You see Jay Baer and others talking about hotel chains. They don’t spend a dime on Super Bowl ads or big campaigns, and yet they manage to stay competitive. They make sure they have amazing customer experiences and those customers in turn become a bigger megaphone than an ad ever could have been; customers go on review platforms and social media and all these different types of individualized channels and do the marketing for those brands. 

That’s what we want to do for our own business and that’s what we want to help our partners do for theirs. We want to help B2B providers be better, and I think we’re in a great position to help with that.

Bio

Dan Olson is co-founder of UpCity, Inc and serves as its Chief Executive Officer. Prior to UpCity, Dan was an early employee and served as Vice President at Performics, the largest search engine marketing company in the United States. He is active in the Chicago startup community and has made investments in U.S. and international firms within security technology and software industries where he can infuse new marketing and operations strategies to unlock incremental value for their stakeholders. Dan graduated from the University of Notre Dame with a Bachelors of Business Administration and a Concentration in Japanese.