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Her Unexpected Elopement Company Is A Runaway Success

"There were stark moments I was very ready to walk away. I’m really grateful for my advisors and friends who reminded me that I was built for this (being a CEO)"

If you think every successful founder or CEO is born knowing that they want to lead a company, think again. Oftentimes the career you end up loving is as impossible to predict as the person you end up loving.

And this founder knows a thing or two about both...

Today's interview is with Hampton member Janessa White, cofounder and CEO of Simply Eloped. Her company organizes incredible wedding getaways for couples and small groups (they've been doing it since before covid made it cool).

It's a combination events + tech business, totally bootstrapped, and generates millions.

My favorite part of her story is the fact that she never even planned to be a founder – her background was in theatre. A perfect example of how entrepreneurs can't be fit into a box or pressed from a mould.

In this piece, she takes us deep into the business, sharing the ups, downs, and really-far-downs (like when bookings dropped 98% in a month due to lockdowns). She also gives us an inside look at what helped her overcome those challenges and build a thriving business.



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

Howdy - my name is Janessa and I’m the CEO of Simply Eloped. We’re the largest elopement provider in the WORLD!

Simply Eloped is a tech-enabled service business, with a soft-end marketplace on the backend. We’re located in 34 destinations in the US and we tackle all of the planning for wedding ceremonies with 20 guests or less. My network of vetted vendors is over 700 and we service 250 venues nation-wide.

To date, we’ve married over 10,000 couples!!!! Also, we marry the coolest people, of all types, as exhibited below:

A Game of Thrones themed ceremony - one of many themed celebrations we've helped organize (Photo Credit: Stephanie Hennessy)

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

The way we, meaning my romantic partner Matt Dalley and I, started Simply Eloped is definitely a unique story. Two months into us dating in 2015, Matt took a trip to New York to do a consultation with a SEO client - Apartment Therapy. He was sitting on a park bench in Central Park and struck up a conversation with a man wearing a bow tie sitting across from him.

Turns out the man was there to officiate a wedding. Curious - Matt started asking a bunch of questions. This gentleman was a New York staple; he’d been an officiant on the tv show Sex and the City; he had been featured as an officiant in the movie Kate & Leopold; crazy enough, he was also a hypnotist. Despite all his amazing experience as an officiant, he lamented to Matt about how difficult it had been to continue finding business since everything had migrated online.

Thus, the idea was born. Whether it was a gripping convo or that Matt had been hypnotized, we'll never know...

When he returned home to Boise, he did a bunch of research and realized there was this whole underworld of folks searching for elopement-related services and no great providers filling that demand. He spent the next 8 months trying to figure out how to help the guy, but the remote nature of the relationship crumbled. Matt was crushed.

I saw how saddened he was and I proposed that we come together and see if we can get the damn thing off the ground. I figured with his experience in SEO and digital marketing, and my experience with wedding coordination, customer service and management, we could be a great team. He was hesitant since we’d only been dating a year, but decided to give it a go. I came up with the name Simply Eloped, we launched a landing page and two weeks later we had our first customer!

The first year-and-a-half, Matt and I organically grew the company just the two of us, which turned out to be a strong choice. We wore all of the hats and built everything the way we envisioned and needed the company to be. One of the strongest decisions we made in those beginning years was to hire a Senior Engineer in Bangladesh to start automating the tasks or duties that we were doing manually. Seven years later, our backend technology (which we lovingly call Central Station) is still one of our greatest differentiators and competitive edges.

Take us through the process of building the first version of your product.

In the initial days of Simply Eloped, I asked a lot of questions to our first customers. I talked on the phone directly with every person we booked and I learned what was important to them. I heard a lot of terms like “personal to us” or “affordable”.

There was a huge gap in the wedding market between City Hall ceremonies and large weddings. The term ‘elopement’ still had a stigma attached to it that echoed from previous generations. Meaning if you eloped it meant that you were in a situation to have a shotgun wedding or there was some negative connotation to needing to do it on the quick.

Couples were hungry to do what felt right to them, despite family or societal pressures.

One of our first logos!

Some things I learned early on about our couples:

  • They preferred bundled packages rather than a la carte services
  • They took ‘stress-free’ very seriously; they didn’t want to have to plan ANYTHING
  • Cost was important to them; they wanted a high-quality ceremony without breaking the bank
  • Having friends and family around them was important, but they preferred 20 guests instead of 200
  • Choosing their vendors wasn’t important to them; feeling like they could trust the company they booked to cover all the bases was
  • One hour of photography was plenty

We took these learnings and got to work on molding an industry. We kicked off in New York City and New Orleans, and leaned on Google search data to lead us on expansion for the rest of our destinations.

We built packages and made it easy to add-on services to those packages. We pushed the rhetoric that an elopement wasn’t just two people - we allowed up to 20 guests with our packages! We made it clear that we personalized EVERY ceremony. We vetted every vendor to ensure they were in alignment with our values and standard of quality.

Early iteration of our website

One of the most surprising elements to me was that we tripped into a soft marketplace. We began building Simply Eloped with the couples in mind, but we had no idea how difficult it was to be a wedding vendor. It’s a small business in itself: marketing, sales, dealing with ghosted leads, processing payments, scheduling, client management, etc.

The way we structured Simply Eloped tackles the bulk of that work so that the vendors can focus on what they SHOULD focus on which is making the couples happy and ensuring their big day is as special as possible!

This business model doesn’t exist elsewhere in the industry so in the beginning it took a lot of convincing to establish ourselves as “not a scam” to potential vendors. 🤣

Form CTA

What we did worked and we grew quickly. From day one, we were off to the racehorses and had a difficult time keeping our feet under us from sprinting so fast.

Bookings the first three years:

  • 2016: $40,000
  • 2017: $300,000
  • 2018: 1.4M

Early Days: Our sophisticated project management system

At this point, the work became overwhelming and we started scaling our team and fast! We began to hire for help with sales and customer management, expansion, PR, admin, etc.

At year 3, we were in BUSINESS! We had definitely figured out our product-market fit, we had begun to scale our teams and processes and things were rocking and rolling! We were running so fast, however, that things started to break down internally. We had a really great idea of what KIND of business we wanted, but this was our first go at it. We were definitely building the train tracks as the train was running at top speed in regards to internal processes, SOP’s, culture, etc.

The first ripple of things breaking down began with our company culture. We had this ideology that if WE were awesome people, and HIRED awesome people, we would just have an AWESOME company culture. When we saw elements of gossip, bullying, lack of ownership, we were shocked! It took us some real time to figure out where we had gone wrong. So, after extracting some people from our company, with our primary advisor we sat down and really assessed some basic elements of running a business:

  1. Hiring - We took a look at our hiring practices and realized we didn’t really have any infrastructure in place for looking for skillset or cultural matches. We really hired based on if we liked the person or not. This was where the heart of our problem began.
  2. Training - Because all of our programs were so unique to us, it was quite a lengthy process to understand what Simply Eloped was all about. We lacked basic metrics or measurements on how to see success in your role or job. We had a lot of work to do here.
  3. Culture - Awesome bosses + awesome people ⍯ amazing company culture. We took some real time to get deep on our values, expectations, differentiating factors and ultimately put a LOT of structure (like in-depth handbook, detailed training programs, detailed job descriptions, etc) that planted seeds everywhere of what we envisioned our company culture being and becoming.
  4. 360 Reviews - We hired a coach to do 360 reviews of both myself and Matt. This was ultimately the healthiest thing we could’ve done. We had become the bosses we wished we had always HAD, instead of the bosses the company really needed. I grew so much from the insights garnered from hiring a professional to do a 360 review.

We were running at full speed already but myself and Matt realized that if we didn’t put these basic pillars in place then we would continue experiencing the symptoms we had been seeing. I’m really proud to say that we took these warnings and acted. The roots of our company culture didn’t start at the beginning; it started here, at year three.

Our first-ever company retreat (Photo Credit: Karen Norian)

For me, the healthiest thing I took away from this period, outside of the need for in-depth and detailed structure, was that not everyone would be happy working for my business. I had found my happy place but that didn’t mean that it would be everyone else’s happy place. From this awareness, I created The Eight 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 ^, 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 he/she needs when feeling like those 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

Even to this day, in year seven, I do the onboarding for every person who starts work for Simply Eloped and I review these tenants, our values and our differentiators. I paint a real picture for each person of what it is to work for Simply Eloped and why it’s so special and precious. I encourage them that if they discover SE is not their happy place in the first two weeks, to let us know so they can continue the journey of finding their ideal work atmosphere. 🤗

Since launch, what has worked to attract and retain customers?

Outside of our tech and culture, we made some strong moves in the beginning that last even to today. Matt’s background was in SEO and digital marketing and so from day one we started refining our strategy in those two departments. To this day, Google Adwords and our organic traffic that’s accumulated from all of the SEO we’ve done over the years are our primary vehicles for acquiring customers.

Our strategy included:

  • Focusing on google ads targeting those searching for elopement services, including geographically based searches like “how to elope in Colorado”
  • Retargeting (which we’ve since discontinued)
  • Utilizing services like HARO to build backlinks
  • Employing writers and contractors to find opportunities for guest blogs
  • For a period of time, pre-pandemic, we did have a PR person in-house who landed us some pretty big PR opportunities

New York Times covered us

Coverage from Business Insider helped change the conversation around elopements

People covered one of our higher-profile elopments

Surprisingly, social media efforts and advertising never really paid off for us. Folks weren’t going to Facebook or Instagram and typing in ‘How to elope’ or ‘where to elope’. They were definitely using these platforms for vendor searches or social proof that we were a legit company, but it rarely turned into meaningful traffic for us.

That is, until the introduction of TIKTOK! For the first time in our company history, we found a meaningful social media outlet that actually drove traffic to our website. It’s been extremely exciting for us to see a platform pay off in this way!

Lastly, as you can imagine, referrals have been powerful for us, both on the customer and the vendor side. Our NPS score with couples AND vendors is over 90 (as opposed to The Knot which is landing at a very sad 8). The proof is in the pudding that both couples and vendors are stoked on the final product of Simply Eloped!

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

Minus the company culture “uh-oh” and definitely some mega trips from running so hard, all seemed bright for our future for Simply Eloped. That was, like many businesses, until that really lovely time hit the globe: COVID. Up until COVID, we were running and running fast! We went from $40,000 in bookings our first year (2016), to almost 3M in bookings in 2019. To say 2020 was off to a really promising start is an understatement.

Then, in one month - March 2020 - we dropped in bookings by 98% and processed thousands of cancellations and postponements. You read that right - THOUSANDS. We made the executive decision to refund deposits of those who cancelled since you never knew what they were going through with family deaths, loss of jobs, etc. We got very lucky with some micro-investments we had taken the year prior and tucked away; that plus PPP saved our company. There were many months we were facing having to lay off our entire company. The fear was real. Like, really real.

However, we took lemons and made lemonade. We’d been running so fast for so long, that our company was kinda messy. You know the whole “run fast and break things” mentality? That was us. We used this calm before the storm to clean house! We sectioned everyone off into teams and assigned house-cleaning projects. We created SOP’s, streamlined processes and systems, refined our technology and user journeys. It was actually a healthy break from our usual grind. We used the time well.

Then, something crazy happened: in fall of 2020, eloping was the ONLY thing you could do. And Simply Eloped was set up for success. If a state closed borders, we could pivot a ceremony to a different state, since we were set up in 34 destinations around the US! We could postpone, cancel or perform a super hot ceremony with very little notice. Overnight, we were back in business and it was awesome.

During this time, one thing started to emerge that we had never seen before: masses of people who had never considered eloping as an option realized what a cool avenue it was! Our industry was becoming destigmatized before our eyes and folks were considering eloping as a third option, in addition to city hall (which all were closed at the time) and large weddings (which were prohibited at the time). That was awesome.

What was not awesome is that prior to the pandemic we were the only fisherman in the fishing hole. Once COVID hit and folks were eager to continue getting married, everyone in the wedding industry was suddenly circling our fishing hole. We witnessed a lot of competition emerge during this time, something we struggle with to this day.

Truth be told, and on a personal note, this is also where my romantic relationship began to fall apart. Being an introvert, I thrived during the pandemic. I was so proud of how we bounced back as a team and I didn’t struggle with the lockdowns. Matt, on the other hand, really struggled. He bore the weight of our potential demise and had a hard time shrugging it. Over the course of the next year after the pandemic hit, the differences of our personalities and dispositions became more amplified. When you’re burnt out, you burn everything. In 2021, we took a trip to Tulum, got engaged, he stayed behind, and we broke up a week later. Oofta - after 6 years of being together, and 5 years of building a business, we ended it all over Zoom with our couples therapist.

This catapulted us into the second time I thought Simply Eloped may bust. It was really emotionally difficult to run a wedding company when you were finally on the verge of getting married yourself. There were stark moments I was very ready to walk away. I’m really grateful for my advisors and friends who reminded me that I was built for this (being a CEO) and that walking away is an emotional decision I would ultimately regret later down the road. They were right.

After the breakup, we spent 6 more months together running the business side-by-side. TLDR: DO NOT RUN A BUSINESS WITH YOUR EX. It was a rough time in all aspects. Fall of that year, I took a vacation to do some soul-searching and landed on how adamant I was about him exiting the business and me sticking in it for a long run. I returned from that trip with clear intention: to negotiate him out. Thankfully, we landed on a deal he felt good about.

Another couple's unique elopement (Photo Credit: Karen Norian)

How are you doing today and what does the future look like?

I’m proud of how far we’ve come as a company, but we have a long future ahead of us! In Matt’s place we hired a COO, Russ Montague, who has been my sidekick since the moment Matt swept out. One of the best decisions I’ve made in the last two years was hiring Russ! To date, we haven’t been an incredibly profitable company but I can proudly say this is the first year we’ll be turning that corner. Here are some fun stats to mull over about the current state of our business:

  • We bring in an average of 60,000 users to our site on a monthly basis
  • Autobooking (meaning someone books our services without ever talking to a sales rep) currently accounts for 30% of all bookings
  • Our AOV is $2500 (and growing)
  • 45% of our traffic is organic
  • Our NPS score for both couples and vendors is over 90
  • The elopement and microwedding industry has grown from 2% of wedding industry in 2020 to 14%! Fast growth!
  • To date, we’ve married over 10,000 couples 😊

My adorable team now

We’ve got some lofty goals in front of us that I’m really looking forward to including redesigning our entire website, going global and really investing in content creation. We may be a 7-year old company, but I feel in my gut we’re just getting started! The industry is finally catching up to us.

Yeah, we do yachts too (Photo Credit: Karen Norian)

Through starting the business, have you learned anything particularly helpful or advantageous?

One of the best pieces of advice I was given early on about being a CEO is to see the business as an organism outside of yourself - something that is living and breathing on its own. By doing this, I’ve been able to detach myself emotionally (as much as is humanly possible) from the roller coaster that IS building and running a business. In seeing Simply Eloped as something that is alive and has needs, I’ve been able to mold the question of strategy in a very particular way: “What does the business need?”. Every stage of the company has required different things of me and my team. I do ultimately feel it’s my job to keep the finger on the pulse of this biz and ensure I’m always doing the best for it based on where it is and what it needs. It’s been my north star and I feel it’s worked out pretty well for me and the business!

What platform/tools do you use for your business?

Tools we use include:

…and many, many more.

Advice for other entrepreneurs who want to get started or are just starting out?

I’m a big believer that a series of tiny steps makes giant leaps! When I was going to school for a Bachelor of Theatre Arts NEVER in my wildest dreams did I think I’d be the CEO of a multi-million dollar company. However, my program was extremely well-rounded and as I was learning how to be a director, stage manager, set designer, etc. I was also building my personal foundational skills for becoming a leader.

If you look at the entire historical makeup of Simply Eloped, it’s just a series of small steps: automating the manual tasks I was doing with our own proprietary tech; hiring one person at a time to take over the roles or duties myself or Matt were performing; launching one destination after the other; doing our very best with every ceremony we perform to ensure it’s their MOST special day ever. Now, seven years later these small steps have added up to us being the largest elopement provider in the world with unparalleled tech (in the wedding industry, at least).

Little by little, we've come a long way from that early website

I love the quote by Goethe:

Whatever you can do or dream you can, begin it; Boldness has genius, power, and magic in it.

So my best advice: just begin.

Are you looking to hire for certain positions right now?

We are currently hiring for fractional CTO and Head of Product. SEND EM MY WAY! 😂

Where can we go to learn more?

Personal links:

Business links:

Personally, I find being the CEO of a startup to be downright exhilarating. But, as I'm sure you well know, it can also be a bit lonely and stressful at times, too.

Because, let's be honest, if you're the kind of person with the guts to actually launch and run a startup, then you can bet everyone will always be asking you a thousand questions, expecting you to have all the right answers -- all the time.

And that's okay! Navigating this kind of pressure is the job.

But what about all the difficult questions that you have as you reach each new level of growth and success? For tax questions, you have an accountant. For legal, your attorney. And for tech. your dev team.

This is where Hampton comes in.

Hampton's a private and highly vetted network for high-growth founders and CEOs.

See if you're a fit...

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