This Founder Failed Forward and Managed to be Acquired by her Dream Company

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. 

Mistake 1: At first, we had no idea what we were doing in regards to hiring, onboarding or training

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: 

• Got nitty gritty on our job descriptions and who our dream candidate would be based on those JD’s
• Created specific interview questions that correlated directly to skillset and desired employee attributes
• Threw out the concept of “just want nice, hard-working people” and drilled down what kind of person we DID NOT want to work for us (sometimes you learn more from what you don’t want, to then build on what you do want)
• Got super cozy with Standard Operations Procedures (SOP’s), documentation and putting all things in writing
• Become very specific with the benefits and consequences of doing (or not doing) one’s job

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. 

Mistake 2: We slept on company culture early on

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: 

1. Built & distributed our employee handbook - we made a guide of all things US, the Simply Eloped way. From how we wanted others to give personalized feedback, to how we felt about swearing (highly encouraged) we illustrated the world of Simply Eloped on how to function in it. We built our mission, vision and values. This acted as a guide book of what we were building and how to behave.
2. Mandated the Impeccable Agreement - accountability was an area we really struggled. Unfulfilled promises that would go unnoticed for months. In response, we put in place the impeccable agreement and we’ve never looked back. If a person broke the impeccable agreement more than 3 times, it was clear they were not a great match for our company. Here’s the structure we put in place: 
   1. Ensure the agreement is clear - who is the owner, outline of tasks or duties, assign a deadline and designate who will plug the agreement into Asana.
   2. Create the Agreement - The owner will plug into Asana and title, outline tasks or duties in clear format, designate owner or owners and assign a deadline.
   3. Follow-through or re-negotiate - Owner of agreement will either complete the tasks or duties OR will follow up with the person with whom the agreement was made to re-negotiate the agreement and change the deadline if need be. Re-negotiation must be made PRIOR to the original deadline.
   4. If agreement is broken, the owner will take responsibility without making excuses. The goal is to rarely or never break agreements.
3. Crafted the 8 tenants of a person who thrived at Simply Eloped - because severe symptoms like gossip and laziness had reared their ugly heads, we felt the need to get super specific on what kind of person WOULD thrive at Simply Eloped, crafted on the person we felt did not. These, to this day, are one of my favorite pillars we’ve put in place. I present to you, the 8 tenants of a person who thrives at Simply Eloped: 
   1. Is passionate about our values; knows that we are adding something important to the world
   2. Wants to contribute to an entity that is fast-growing and dynamic
   3. Because of this, is flexible, willing to pivot fast and work in an ever-changing environment
   4. Is hungry to learn; hungry to grow themselves
   5. Desires a leadership team that truly cares about them, their needs and goals
   6. Is willing to ask for what they need when feeling like their needs/goals aren’t being met in the SE atmosphere
   7. Handles issues/problems productively and constructively
   8. Can envision the place in the world SE will continue to fill and grow into, and therefore wants to work hard to get it there

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.  

Mistake 3: Chasing the shiny object

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!

Mistake 4: Heavy on trust, modest on verify

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:

1. If used properly, data is an effective and easy way to measure performance. My favorite aspect of it is that it’s not something one can easily refute and is difficult to take personally. We struggled with our source of truth, and had a lot of data debt, making it difficult to measure company or individual performance. Looking back, I would’ve invested in this a lot earlier to ensure we had data integrity company-wide and used it as a vehicle for measuring performance.
2. It took me many years to learn but not everyone needed or desired me to be the kind of leader I had longed for. I now know part of being an effective leader is being able to adapt to what my team needs. 

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. 

 Mistake 5: Assuming What Did Work Will Always Work

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: 

• Leaned more into markets that weren’t as popular with other vendors: our competition really emerged in places like Hawaii and Colorado, but we were in 34 destinations in the US! We refocused some of our marketing efforts to really focus on the lesser competition markets to make more of a boom. 
• Launched new programs: We experimented with new offerings like picnics or luxury elopements. 
• Overhauled our website and branding: When you’re a company around for 8 years in a tech world that’s ever-changing, you’ve got to ensure you stay with the times from a UI and branding standpoint. We invested in updating our website and branding to keep up with all of the emerging trends and competitors. 
• Experimented with new platforms: We launched our brand on Tiktok and saw a lot of benefit from this platform. While it didn’t convert into customers, it was amazing for brand exposure and on-site engagement. 

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. 

What we did right - the turnaround

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: 

• We listened to our customers (our couples) - from day one, we had our ear to the ground of what our customers wanted. From scouring google search data to one-on-one conversations with leads, we listened and constantly refined our product based on feedback we were given. 
• We invested in our SEO. We knew we couldn’t hang with the heavy champs from a paid marketing standpoint, so we invested heavily in PR, backlinks and relationships with reporters to continue building our domain authority. It worked and to this day we regularly emerge in the top three positions for attractive elopement-related search terms. 
• We built out a behemoth piece of tech. Our bespoke technology acted as insulation. Our product was easy to model after from an elopement standpoint, but our tech remains to be our secret-sauce and the vehicle to enable us to deliver on thousands of elopements on an annual basis. Also, the custom build vs no-code build made us more attractive to big buyers as it was more difficult to replicate. 
• We pivoted on a regular basis. You hear it in the startup community regularly, but the ability to shift and pivot based on what the market is doing is a real superpower. As things started changing after COVID, Simply Eloped continued to listen and maneuver as things shifted. 
• We prioritized relationships. The world of being a founder can be really lonely, even with a co-founder. I found the people I surrounded myself with during my lightest and heaviest moments really shaped the type of founder I became. Fast-forward eight years later and some of my best friends have developed from the founder relationships I formed. Shameless plug - this is part of the reason I believe so much in the Hampton model: no one understands your journey like someone else going through it or someone who HAS gone through it and Hampton has founders at every stage. Relationships like this can transform your business at key moments, as I’ve witnessed at multiple stages through my business. 

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

Where can we go to learn more?

Simply Eloped's website
Instagram
Tiktok

Where Janessa can be found:
LinkedIn
Tiktok