In the last ten years, Chrystie Vachon started and sold six websites. She’s also been a consistent trend spotter, like when she went all-in on Tik Tok, going viral to the tune of 1 million+ views and 40,000+ subscribers—after uploading just 10 videos.

Chris Schelzi sat down with Chrystie to tease out the business lessons she learned—and business mistakes she experienced—along her entrepreneurial journey.

Scramble for the closest notepad. Here’s their conversation.

Business Lessons Chrystie Vachon Learned from Building & Selling 6 Websites

When and how did you start your entrepreneurial journey?

Chrystie started her first website in 2005 as a passion project dedicated to celebrity gossip.

By 2007, the site boasted 500,000 monthly visitors, which she monetized through ads. But Chrystie started losing interest. She’d just had her second child and didn’t want to pursue things with the website any further.

So she sold.

A year after the sale, the new buyer resold Chrystie’s old website for 10X what they’d paid Chrystie, after having made almost no changes to the site.

She had no idea her website could have sold for so much. But that experience made Chrystie aware of an underlying opportunity: She could do it again.

Chrystie realized she’d found a repeatable business model. She’s since created and sold 5 more websites over the years. Here are a handful of lessons she’s learned along the way.

How to overcome Imposter Syndrome

Chrystie had her biggest website sale in 2015. It was a personal finance and couponing site she’d launched in 2010. In those five years, she managed a team of 7 content writers and even garnered televised publicity as a couponing expert.

Despite all the success in her market, Chrystie felt like an imposter.

Couponing was a crowded market at the time. Her competitors seemed so much more knowledgeable about the subject. How could she compete?

Fortunately, Chrystie has a tried and true elixir for imposter syndrome: Hosting in-person events.

Chrystie explained that when she’s deep in a crowded market, it feels like every topic has been covered a hundred times. When you’re steeped in that world, it can feel like everyone knows all there is to know.

But hosting in-person events plops you back to reality. Most people probably aren’t familiar with the intricacies of your field. Old ideas in your industry are still novel to someone unfamiliar with your subject.

Hosting in-person events forces you to realize the true expertise you carry.

How do you enter a crowded market?

Remember that no two people are alike. Everyone brings their own experiences and angles, even to old topics. Each of those experiences presents a new opportunity to relate to and communicate with a different group.

If you are entering a crowded market, start by researching the biggest brands and thought leaders in that space. What’s missing from the larger conversation that you can add? What makes your product or brand different?

Don’t be afraid to enter a crowded market.

Describe a situation in which you had imposter syndrome. Were you able to push through and feel more confident in your abilities in the end?

You have to know 10% more than another person to be a helpful teacher. Start writing, teaching, and speaking about what you know. The only way to know if there’s room for you in a crowded market is to start building and teaching.

What’s your biggest weakness in business?

One of the benefits of having built so many businesses is Chrystie’s learned self-awareness. She knows her entrepreneurial strengths and weaknesses.

Chrystie recognizes, for example, that she’s great at starting projects. She has a track record for turning ideas into profitable action.

But she admits that her strength is bookended by a weakness: a habit of selling her businesses instead of building the necessary processes that would enable her to grow larger businesses. As Chrystie put it, she’s built multiple six-figure businesses, but has never waited long enough to scale a business to the 7-figure level.

In part, she blames her tendency to ride the wave of trends. When she’s hooked by an idea, she rides the wave. When she’s “done” with the business, she jumps off.

The downfall to this approach is that she’s trying to time the market instead of building businesses that last.

In the case of her couponing site, Chrystie realizes, in retrospect, that she rode her website a couple years past its pique. While it’s still her biggest website sale to date, she believes she waited too long to sell.

Chrystie says she’s done chasing business trends, but she still believes in using trending platforms—like Tik Tok—to market her ideas.

What’s the ONE business lesson you’d give?

One of the most important things you can do for your business idea: move, act, progress.

It’s easy to get caught up wrestling with questions in your head. Instead of taking action steps, entrepreneurs get stuck in research mode. They overanalyze when they should instead just give their idea a try.

Chris recommends putting your research season on a deadline. Give yourself a week to take courses, read existing blogs, and learn more about the business idea. Then, you’ve gotta move.

Action item: If you have an idea but are unsure where to begin, Chrystie recommends getting feedback from friends and family about your business idea. Then apply the 5-minute rule: What can I do in 5 minutes that can move my business forward?

How do you know if a niche is too small?

The first thing Chrystie does when she has a business idea is look online. She wants to get a sense of who else is already doing that same thing. If others are doing it, that’s a good sign. Look for ways you could be different from what’s already on the market.

If no one is doing it, that’s a red flag. It means people have had your idea before, but went into oblivion because the idea didn’t work.

If you’re interested in a niche, just go for it and see what happens. Locking yourself into a small niche doesn’t have to be a problem. You can start in that niche and pivot into larger ones if you find the original was too small.

Start by validating the smaller idea.

Take action to see if it’s monetizable.

Should you double down on strengths or weaknesses?

Simple answer? Yes.

Do both and take the hybrid approach.

As an entrepreneur, you should always be expanding your abilities. Even if you never apply your weaknesses professionally, you should know enough about that subject to be able to hire someone who truly knows what they’re doing. In order to outsource well, you must have an eye for quality and mastery.

So: double down on your strengths and learn enough about your weaknesses to tell the difference between quality and inferiority.

Bring someone onto your team who can also teach you the basics of that skill you lack. Learn their systems. Try to overcome the things that challenge you.

Bring in people who are smarter than you and be open to learning.

How did you land your position at AppSumo?

Chrystie was working at a different startup in Austin. A recruiter reached out to her on LinkedIn. At the time, she wasn’t looking to take a chance. But she later was ready to make a move. Chrystie contacted the recruiter again and said she was ready to join AppSumo.

The rest is history.

Any tips on getting visitors to your website?

Content.

Content is your #1 play. Any article, social post, or video can introduce potential customers to your business by bringing them to your website.

Go out and create as much free content as possible. Make it across social media, your website, YouTube, etc.

Focus on two types of content:

1. Content on your website or blog
2. Native content for outside platforms like YouTube, Instagram, and Tik Tok

Speaking of Tik Tok… Is it worth your time?

Chrystie gave a resounding yes.

Two of her videos have already hit 1 million views and she’s only uploaded 10 videos so far.

The key to creating content on any platform is to tailor it for the medium. This is true for Tik Tok as well. Start experimenting. Jump on that early traction to grow your following. Worry about converting that following into customers later.

When are you running for president?

“Never!” – Chrystie Vachon

How do you get more comments during live videos?

It’s very easy. At the beginning of the live video, ask people where they’re from and what they’re doing today. If you get people typing at the beginning, they’ll be more engaged throughout the whole live video.

Have you ever hired a business coach and do you recommend them?

Chrystie hasn’t hired a business coach but said that if she could go back, she would.

Business coaches help you move faster. They help you put business processes in place so that you gain traction faster, which inspires you to move even faster. It’s compounding in that way.

The trick is hiring the right business coach.

Here are some questions to ask a coach before you work with them:

• Have you worked with someone in my niche before?
• What were your results?
• What details will we discuss in each of your meetings?

It’s important to work with people who’ve worked in your space.

A huge thanks and shoutout to Chrystie Vachon for sitting down with AppSumo for this conversation.

Want to get more exclusive content for running a business from home? Check out AppSumo’s FREE live Remote Work Academy for the next few weeks! Register here.