SureSwift Capital acquired HelpTeaching, an Education Technology platform for teachers, tutors, and homeschooling parents with more than 1 million global members in 2015. Lilia Tovbin, who co-founded the business shared her story with us recently including what it was like to scale a business while working a busy, full-time job, why she decided to sell a company she considered her family business, plus her latest business venture.

An Interview with entrepreneur, and HelpTeaching Founder, Lilia Tovbin

What was the #1 reason that you decided to start your own business? Were you doing it as a side project, or was it your full time gig?

My first full-time job was at a dot com startup. It was a company called “Bolt” that was like an early version of Facebook. It was an amazing experience. We had stock options, a great team, game nights, off-sites at Six Flags, the CEO would make us smoothies… the list of perks was seriously endless.

So when a colleague from that job approached me with an idea to start a business I jumped at the opportunity. I was in my mid-20s and on the lookout for opportunities to start something on my own. I dreamed of employing people someday and recreating that feeling of an awesome place to work.

How did you know it was time to make your first hire? What role were you looking to fill, and where did you go to find that person?

My business was in the Ed Tech space and I had no background in education. One of my original co-founders had extensive experience in the field, but when our founding team lost momentum after 3-4 years, I bought out the business from my 2 other co-founders before it reached any scale.

The platform included member-generated content, and I was moderating it with my limited expertise. When my moderation queue blew up into the tens of thousands of review items I knew I needed to hire help.

I posted a job on Craigslist in the local area, but one of the strongest candidates was a couple states over. She was such a good candidate I decided it didn’t matter that I couldn’t meet her in person. I hired her and a couple other non-local freelancers around the same time. I ended up working with all 3 of my first hires for over 6 years! That was the beginning of my fully remote team.

Once you had money coming in and you knew this product just might work, what was your goal? Was it hitting a certain Monthly Recurring Revenue number, was it selling the business? Tell us a little about what your plans were once you saw that HelpTeaching could generate real revenue.

The goal was always to make enough money to be able to give up my full-time job, which was challenging because as a developer I was making good money. By the time I bought out my co-founders I was in a leadership role with NYTimes.com and I was making 6-figures.

“The idea of becoming a full-time entrepreneur is very appealing, but it can take a long time, and sometimes a leap of faith to make it your reality. Click to Tweet.

The business was a side project on top of my day job for 8 years before I made the leap into a full-time entrepreneur role. I didn’t mind the long hours because the business was my passion project, but it did feel like the two jobs were a distraction to each other, and I needed to focus on just one career path.

Eventually I had a 6-figure income from both my day job and my business, and it was obvious that I had to make a choice. I quit my day job in 2013 to focus on HelpTeaching full-time. Once I focused on the business full-time the growth rate climbed into 3-figures and maintained that pace until the exit, but I had been working very long hours for a lot of years at that point, and was ready to slow down. When I realized a sale was possible, I knew it was the right decision for me.

At what point did you know it was time to sell HelpTeaching?

I had no idea that selling a business with less than a million dollars in annual revenue was even possible. I thought of it as a “family business” that I would be owning for a long time, so I built it with long-term goals in mind.

When I was approached by a broker in 2015 and realized a low 7-figure exit could happen it kind of blew my mind. I wonder if the founders of businesses at a similar stage understand that an exit is an option for them. I feel really empowered to share my story and SureSwift’s when I talk to other business owners because of that. Founders have many reasons to sell a business, and it’s good to understand your options and have a strategy for a startup exit as early as possible to be prepared.

Tell us a bit about the process of selling your business. What were you looking for in the selling process? How did you know who to trust?

Honestly, it was a stressful experience for me. I don’t think the broker I worked with did a great job of managing expectations (on both sides), or with facilitating the actual transaction. I ended up extending the Asset Purchase Agreement myself in an attempt to cover more conditions and clauses, as well as creating an asset list.

In 2015 SureSwift was a pretty new company — it didn’t have a big online presence or established reputation like it does today — and I felt uneasy about not getting the entire sale price on the closing date and having some of the money locked until the end of a 3-month transition period. It felt like I needed an iron-clad contract to ensure I got paid the final amount.

In spite of my concerns, I was ready to move on to my next venture, and following the sale, SureSwift brought in a support person immediately, so it was great to be able to shift my focus from day-to-day operations and time-sensitive work to more strategic work. I wound up staying on as a growth advisor for other businesses across their portfolio.

I should note here that I was one of the early businesses SureSwift acquired, and since then we’ve really formalized and improved the acquisition processes with Letters of Intent, Asset Purchase Agreements, a Turnover Guide, and better communications all around. So while it wasn’t easy at the time, we were able to work together to use my experience as a way to make things better for future sellers.

Now that your business has been acquired by SureSwift Capital, what were/are you hoping for with the future of HelpTeaching?

I wanted to be sure that the people I had hired could continue to work with the business, and that it would be a good place for them to work. Some of my long-time freelancers were concerned about new ownership, so we put new agreements in place to ease their minds. The business was growing at 3-digit pace year-over-year prior to the sale, so I wanted to make sure new revenue (vs. renewals) didn’t collapse after the transition period when I would be less involved.

What are you working on now?

After the support period for HelpTeaching ended, I was asked if I was interested in working with some of the other B2C businesses in the growing SureSwift portfolio and I happily jumped on the opportunity to put my marketing skills to the test on other businesses.

SureSwift acquired two additional Ed Tech businesses in 2017, so I’ve been helping out with the strategy across that segment of the portfolio, as well as advising on the marketing strategy for some of the other businesses.

Over the last few months my focus has been shifting to acquisitions and marketing for the SureSwift brand, and I’m excited to be a part of the process that enables dream exits for founders like me and brings great products into SureSwift’s family.

One of the reasons I sold HelpTeaching to SureSwift was also my desire to move on to another project I had already started working on with the same technical co-founder. He had built a tool for sending bulk email campaigns via Amazon SES at a low cost for HelpTeaching newsletters and we wanted to grow that into its own business. And this exciting journey from B2C Ed Tech into B2B SaaS was possible because of my previous successful exit.

You can find out more about Lilia's next venture in her recent interview with Maker's Mag, or follow her on Twitter @webbie.

You can find out more about Lilia’s next venture in her recent interview with Maker’s Mag, or follow her on Twitter @webbie.

What’s your best advice for fellow entrepreneurs?

Now when I talk to fellow founders and entrepreneurs, I always stress the importance of preparing your startup for an exit from the very beginning. Because you really never know what will happen with your business, or your life, and there are so many reasons to sell a business that it’s crucial to create a plan.

That way you have options — whether it’s starting a new project, starting a family, or just taking a breather from the hard work of being an entrepreneur. It’s something I wish I had done sooner, and something you’ll never regret.


Co-Founder and CEO of SureSwift Capital. We acquire and operate successful technology companies.Kevin McArdle | CEO, Co-Founder Kevin is the CEO and Co-founder of SureSwift Capital. His passion for personal relationships and driving business results are at the heart of SureSwift’s impressive growth to date.

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