There are many things one can do to prepare to be a business owner prior to launching a startup and Janessa White, the co-founder of Simply Eloped, did none of them. Despite every pitfall and hiccup, she pulled off a miracle and recently sold her company to her dream partner: The Knot Worldwide.
You can read the origin story of Simply Eloped in our previous feature here. This one is much different. In an effort to help others not make the same mistakes, Janessa unveils everything she did wrong in the early days…and how she still managed to build a successful business, leading to an acquisition.
Here's the story straight from her.
I never set out to be a business-owner or startup founder. My background was in theater and I was convinced I would be in the rehearsal hall or the stage as long as I could stand. My life took a sharp right turn when my romantic partner at the time, Matt Dalley, came up with the idea of an elopement company. Seeing our adjacent skill sets and our combined passion to build our own endeavor, I hopped onboard and we launched ourselves into startup land.
An advisor of ours recently reflected on the 8 years we spent building Simply Eloped and remarked that this business was our foray into startup school - and he wasn’t wrong. As a founder, I made every mistake one possibly could, and still managed to see the exit of my dreams. Consider this your playbook of what not to do when building a company from the ground up.
For the first year-and-a-half of our business, Matt and I wore every hat/worked every task. We managed to scale from zero to nearly $250,000 in revenue before hiring a single employee. The only reason we even hired our first employee was because we lost our phones in the ocean while we were working abroad and needed someone to run our social media (this was well before social media management platforms existed).
Our first employee quickly evolved from running social media, to aiding me in customer experience to then preparing to onboard CX employees and managing those new hires! Due to the quick nature of our growth, we didn’t put any of the proper pillars in place to ensure we attracted, vetted and hired the best people for our teams. Our attitude was that if you seemed like a nice person and a hard worker - we wanted you!
Fast forward years later, when we were running into unexpected cultural symptoms, we were finally called out on our poor interviewing, hiring and training practices. With this clear “aha” we got to work in crafting infrastructure to ensure a more fruitful process we:
After this aha and putting some of these practices in place, we felt we’d made a ton of progress as startup founders and managers. Sadly, these weren’t enough, we soon came to find.
Soon after scaling our team, when we started receiving reports that gossip was running amok in our business, we were shook. “But we’re nice, hard-working people!” we remarked. How could we possibly have these symptoms when we did nothing to create these problems?
Because even with infrastructure in hiring, interview and training, we had completely overlooked investing in our company culture. Our assumption was that if we modeled the behavior, thus the behavior would be exhibited. Oofta - we were we wrong.
Yet again, we were faced with having to drill down on a problem that didn’t seem core to building our business, so that we could get on with building our business! We implemented three things that helped immensely:
It took us a lot of focus, effort and time to create good practices for hiring, interviewing and onboarding. It took us even further down the rabbit hole to drill into what we wanted our little world of Simply Eloped to look like from a cultural viewpoint. We felt we’d just gotten our feet under us, when the world imploded and COVID hit. Everything changed for us from there.
When you’re building your own product, it’s really easy to lose sight of priority. We were a (mostly) bootstrapped company and therefore never went out and raised traditional capital (shoutout to our primary investor Indie.vc who is indeed the most founder-friendly early-stage capital out there!). Because we were strapped, we did our best to grow our own tech, which we lovingly call Central Station, as quickly and organically as possible. In the beginning, we had great focus on what to build and why: we prioritized automating my time as quickly as possible so we could scale out our CX teams. In the beginning, I was manually building contracts, invoices, itineraries, etc. We chose one at a time and automated my processes, thus building the foundations for customer experience superheroes.
However, the deeper we got into the business, the easier it became to chase the shiny object. Instead of backing up our fun ideas from jam sessions with data, we made decisions based on gut feelings. It also became quite easy to prioritize the newest and most exciting idea instead of sticking to quarterly or sprint planning. This created a mess of our roadmap: we would be halfway through a project, scrap it and start building the newest and most fun idea.
Not only would we constantly and consistently pivot, but because we didn’t back up our theories with data, we’d spend months building something only for it to fall flat on its face immediately upon launch.
My favorite product feature that worked out amazingly: Auto-booking. To this day, we’re one of the only wedding companies where you can book your date, destination and package without talking to a single person. Currently, auto-booking consists of 30% of our overall bookings.
My least-favorite product feature that totally bombed: Select-a-vendor. We had a theory that we could open up our value offering to a much wider audience if couples could choose their own vendors. We invested six months into building a tool where a lead could view and select their officiant, photographer, hair & makeup artist, etc. Weeks after we launched it we had several customers cancel because they felt confused as to why they hired us in the first place. There was a strange psychology that if they chose their own vendors, then we weren’t doing any work. Feature bombed.
Ultimately, our tech platform—Central Station—has become one of our secret powers. Not just a CRM, this technology powers everything we do and enables us to plan not hundreds of ceremonies per year, but thousands!
If we’re leaning into vulnerability, this is where I’ve grown the most as a leader. Similar to the lack of infrastructure we had in hiring, interviewing and training, as a company we really lacked in how to measure performance. We definitely looked into models like EOS, but felt we could take bits and pieces instead of implementing the whole program.
There are huge benefits to being a trusting leader! It can create a great sense of team and togetherness. It also exhibits to your employees that you trust them to perform and manage oneself. As a manager, I always worked to be the type of leader I had always craved; one that gave me the breadth and trust to perform at the pace that was in-step with what I was able to achieve. We invested a lot into ensuring that our team felt like we cared about them as people. However, there were two extreme gaps in my understanding in how to be a great leader:
For me, I always interchanged the act of verifying with being a micromanager. I now see that it’s just a key tenant to ensuring everyone knows what their job expectations are and how they’re living up to those expectations. Data has become my friend and I’ve really enjoyed the process of getting deeper into the weeds with understanding how micro-levers can drive great things forward.
We had a huge competitive advantage before COVID hit: elopements were underground. To a degree, they were still stigmatized. Think shotgun wedding or marrying in secret. A lot of our audience, at the time, were second weddings and same-sex ceremonies. By the time 2020 rolled around, we were already set up in 34 destinations and had performed thousands of weddings! We had invested a lot into SEO and PR, so that when an individual searched anything elopement-related, we were at the very top.
While we had run fast, we hadn’t run fast enough. COVID hit and overnight we had thousands of cancellations and postponements, all of which we graciously refunded deposits or pre-paid invoices back to couples. We had a three month stint of no action, since the world was on pause.
Fall of 2020 we suddenly saw a boom and eloping was all you could do. Having 34 markets really helped us, because if one state closed borders we could easily pivot to another. We were suddenly at the race-horses and we were back to full speed!
What we didn’t (and couldn’t) anticipate was just how much competition would emerge at this time. Our analogy is that for four years we had the luxury of being the only fisherman in the fishing hole and overnight all the other fisherman flocked to our hole. It suddenly became much more difficult to catch lunch.
Being a startup means pivoting and we shook up our strategy to keep up with the times. Here’s what we did to keep up with the changing times:
The events of COVID were a healthy reminder for us that what worked historically, won’t always work moving forward. It was paramount for us to keep up with the times and continue listening, gauging and assessing whether or not our offerings still had the product/market fit we did in the early days. You know how they say with parenting you feel like you finally “get it” and then your kid changes? Well, it’s the same with running a business. If it’s not keeping you on your toes, you’re likely not doing it right.
Despite all of these missteps, falls and head-on collisions, you don’t catch the attention of a big company like The Knot Worldwide, without doing one or two things right. I could talk forever about everything we’ve done wrong to get us here, but we ultimately did a lot of things right as a company and built something I’m genuinely proud of. Here’s a snapshot of a few things we did right to ultimately get us to the exit of our dreams:
Building a business from the ground-up is grueling, difficult and sometimes downright painful, but the growth that comes out of such an endeavor is priceless. I broke my back for this company and genuinely sacrificed 8 years of my life to go to “founder school,” but it was one of the most fruitful experiences of my life.
May 21st, 2024 was the magical day Simply Eloped went from being a lone wolf to being a part of the tribe of The Knot Worldwide. Not only did we invest a lot to get the company to this stage, but we invested years cultivating a relationship with The Knot so they knew who we were, what we were about and what we were constantly working on.
My biggest tip: target who you want to buy your business early on and get a foot in the door. Build relationships with the people in charge of or connected to those who would be in the decision-making role to acquire your business. Acquisitions certainly don’t happen overnight and thus plant the seeds early so you can see the fruits later down the road when you’re really making waves.
The Fahrenheit 451 group from Hampton at Carbone’s in NYC
Simply Eloped's website
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Where Janessa can be found:
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