Lessons Learned Bootstrapping Obvious.ly to 100 Employees + Exit

I can't tell you how much Hampton member Mae Karwowski sold her company for. She can't tell you either (because of the lawyers).

What I can tell you is that during one of the darkest hours in the business – when covid had rocked the industry, and she was trying to run the (newly remote) team on unreliable wifi from a cabin in the woods – at that moment, she had an offer for $25 million on the table.

"I turned it down knowing we were worth significantly more and we would pull through this," she says.

That bet ended up being very, very right.

So until the NDA lapses, this piece won't have any numbers in it. What it does have is incredible insights from one hell of a founder who bootstrapped a team to 100+ people before a successful exit, and did it her way. 

In the following sections, Mae goes behind the scenes to unpack:

• How she came up with the idea for Obviously and landed her first client
• The habits that compounded to give her team an unfair advantage
• "Oh shit" moments that only another founder will fully appreciate
• Strong beliefs she holds on leadership, and how those play out day-to-day
• How she knew it was time to sell, and what she learned from the acquisition
• Where she still sees untapped opportunity in the creator economy
• and more...

Hello! Who are you and what business did you start?

Hi, I’m Mae Karwowski, CEO and Founder of Obviously, the leading tech enabled influencer marketing agency. 

Using our proprietary technology and data, we build global networks of creators for the world’s biggest brands; from Google to Ulta to CVS and Dominos. It’s an awesome company to build and lead! We partner with creators who have very small (1,000 followers) to mega celebs (100M+ followers). 

After bootstrapping the company for 10 years, we had an incredibly successful exit to WPP this spring.

What's your backstory and how did you come up with the idea?

I started the company out of my Lower East Side apartment  in NYC with a few thousand dollars in my bank account. I really tapped into the strong network I had built in the city from working at Gilt, start ups and helping friends with their social strategies for the companies they were launching.

I had A LOT of ideas around how to best utilize social media to stand out and win as a brand. And I knew social media had the potential to change the fabric of our culture. 

The idea I was willing to base everything off of was the concept that brands should be collaborating with social media creators who are awesome at growing their own audience organically. And brands should be building relationships with thousands of the right influencers for them, and doing it on a global scale. 

This was something that was NOT an accepted idea at the time. I got a lot of blank stares when pitching our business, but it’s 100% come to fruition as the influencer marketing industry is predicted to hit $30B by 2025. 

I landed Uniqlo as my first client. At the time their motto was ‘Made for All’ so I pitched that we should partner with 1,000 microinfluencers instead of one mega influencer like Kim Kardashan (everyone wanted to work with Kim K at the time.) 

They went for it and we sent out 1,000 airism tshirts to 1,000 influencers – from grandmothers, to skater-kids, to restaurant owners, to fashion models. It was awesome! It also was incredibly difficult to coordinate without technology and do it all manually.

We hired several interns (one of whom is now our excellent VP of product, Ashley Buchanan) and worked around the clock to reach out to 1000 ppl manually. Knowing this was a huge problem to solve, I brought my co-founder and Chief Technology Officer, Max Domain, onboard to build version 1 of Obviously Studio. We were off and running.

One thing I’ve been exceptionally good at has been to understand the customer and their decision making patterns each and every day of building this company. 

I talk to customers everyday and I talk to my teams’ that talk to customers everyday, training them to look for nuance and opportunities. I was early to the influencer marketing party, and hundreds of companies have come and gone since launching Obviously. 

One reason we’ve been so successful is that we know what the customer is ready for, what their qualms are, and where the opportunities are at this moment and 6 months out. That compounds into a huge advantage. 

One small example of that is that we got a warehouse a few years into starting the company, because I realized brands were working with smaller numbers of influencers because they didn’t want to have to stay late many nights in a row mailing packages to creators. If we shipped and designed awesome boxes, they’d happily 10x the number of creators they’d work with. 

Did you ever have an “oh shit” moment where you thought it wouldn’t work?

I was living in a tiny cabin down a mile long dirt road in the middle of nowhere upstate NY with my husband and my parents after fleeing NYC during the beginning of Covid in 2020. 

Most of our clients paused or canceled their contracts, the entire team went remote, and I didn’t have stable wifi so I used $1,000 of cell phone hot spotting to get internet. 

The company was in danger of running out of money. 

I was seriously worried, and just at that moment we had an offer to buy the company for $25M. 

I turned it down knowing we were worth significantly more and we would pull through this and slugged it out for all of 2020 from that cabin. We were flat YoY from 2019. Some very dark days made us strong and those lessons I learned that year truly shaped me as a leader.

When did you know it was time to sell?

This was when 👇

I was tearing up at a pizza place in Cannes France during the Cannes Lions Ad Festival in 2022. I felt the sea change in the industry and knew on a gut level it was the right time to engage. 

The year before I had to sneak into parties and onto guest lists in order to network with the right decision makers. One year later, everyone wanted to talk to me. 

The big agencies had realized (finally) that they needed a real deal solution to address the influencer marketing needs of their clients. I always said that if I decide to sell, I have to be so fiercely sure that I'm not going to waffle on the decision, so hence the tears. It was a big moment and that gut feeling was right on the money. It was amazing timing.

What did you learn from the acquisition process?

An unbelievable amount. You know when you have a conversation with someone and in the middle of speaking you realize you have a vast amount of knowledge on that topic that you did not possess a year ago? That’s how I feel at this moment. 

The biggest take away is that If you are a founder, do a ton of homework on M&A in your field and start early. 

Talk to other founders who have exited and ask a ton of questions. Talk to bankers, M&A people, just consider it part of your job to understand all your options. It’s not ‘getting distracted’ it’s being the best steward for your company. 

Also, with personal investing you hear all the time “you can’t time the market.” Well you can time the market if you are strategic and thinking long term about an acquisition event in the future. 

If I were to start another company tomorrow, I would make sure that the right elements are in place at the outset for an acquisition down the road. Those components of a highly sellable business are one and the same as the components for creating a strong, thriving business from day one. 

Any other advice?

Everyone told me I needed to raise VC money to be a legitimate company. We did not. Everyone told me Obviously had to be SaaS. We did not do that. Everyone tells you to wake up at 5am and take cold plunges. 

Do what makes sense for you and the business you are building. 

Most of our competitors who raised lots of VC money are having a really difficult time now without a path to success or are completely out of business. WPP wanted us because we were a tech enabled agency, not a SaaS company. Most SaaS companies in our space have tried to pivot into tech enabled services like us. 

So think through all your decisions and make sure you own all of them.

What have been the most influential books, podcasts, or other resources?

The hard thing about hard things brad horowitz is a must read for any founder. No one understands the pit in your stomach when you have to fire someone you’re fond of, or have to have a difficult conversation with a client/vendor/employee. The way you approach and handle those tough situations define you as a leader. The training that happens in real time in the midst of doing business is rarely written about so candidly.

And call me quirky, but I love reading books on total business disasters. 

I swear it’s not schadenfreude, everyone starts out really wanting to be successful and comes from a good place. I think there are such gems in these stories when it comes to leadership and governance mistakes. Smartest Guys in the Room - The Enron Story. Cult of We. Bad Blood. Barbarians at The Gate. When Genius Failed. You get the idea. Give me all the mistakes of others and I promise I’ll learn from them! 

I also take the big tech/start up/ entrepreneurship podcasts with a huge grain of salt. I usually zig when others zag, and I’m really wary of group-think. If you’re listening to the exact same thing as everyone else, it’s easy to take a trending opinion as factual. 

Question everything! 

Where do you see untapped opportunity in the market? What business do you wish someone else would build that would make your job easier?

There need to be way better services and tools for creators. 

There was that huge rise and fall of funding in the creator economy. That just became everyone trying to solve the easiest problem - namely paying influencers faster. 

Content creator is now the #1 job listed when high schoolers are asked what they want to do as a career! And the industry isn’t set up to handle all the different needs these kids will have on their path to becoming the next Mr. Beast. 

It is unbelievably hard to create the volume of content day in and day out that many of our creator partners do. I’m in awe of it. And it does have a creative and psychological toll. 

Many people who are incredibly creative (gross generalization ahead) have not also developed a strong business acumen yet. Creators need help in growing strong careers and strong businesses.

What are some strong opinions you have about leadership, and how do you actually put those into practice in your company?

You need to do two (sometimes conflicting) things at once: Inspire confidence from your team that together we are accomplishing great things AND you as a leader are human too, and you are growing and learning on the job. 

To do this you should be constantly highlighting reasons and data to show how we are winning as a team, and if we are failing at something, we are winning at the plan to turn that aspect of the company around. 

You need to be able to understand why you believe something to be true, and explain that reasoning to your team. As a philosophy major in college I spent a lot of time in the classroom doing this and it prepared me better for entrepreneurship than I could imagine. Why do you believe you should raise a series A round? Why do you believe you should do a round of layoffs? If your team understands your thinking it achieves many things: 1) they trust that you’ve considered all viable options 2) they could bring up points you hadn’t thought of 3) they appreciate that you are not a egotistical dictator 4) you’re entrusting them with the ability to think through the situation as well. 

You have to give people the framework to succeed. Candidly This was something I was not good at in the beginning. My thinking: ‘I built this from scratch with zero instructions, my team should be able to too!’ No. They shouldn’t. You are the leader and they need to learn from you. Set them up for success with a proper job description, goals, KPIs, onboarding process, teammates responsible for their entry into the company, clear feedback and performance reviews. Maybe you aren’t built that way, and you don’t need the framework - but hey you’re reading this blog having started/wanting to start a company, and you can’t expect that from 99% of your team. Give them a roadmap and they’ll reward you with completion of that roadmap or a clear indication they are in the wrong role. 

Also one note on leadership I'm still processing, but I became a better leader after I became a mom. I don’t get upset about small things unless they are symptoms of larger issues. I’m faster at explaining my reasoning and setting up more support for my team to do their jobs better. I’m just more focused on defining the top objectives of the business, clearly articulating those objectives, formulating plans to get there, and cutting out any extraneous noise that isn’t helpful. I wish someone had told me that there could be some significant upsides to starting an awesome family while leading this company. 

Where can we go to learn more?
I’m on LinkedIn, my website (with contact info) is here and my company’s website is here.