The 10 biggest mistakes I made bootstrapping to $1M ARR
How Melissa Kwan built eWebinar without an abundance of resources or friends in high places
👋 Hi, it’s Kyle Poyar and welcome to Growth Unhinged, my weekly newsletter exploring the hidden playbooks behind the fastest-growing startups.
I’ve been a fan of Melissa Kwan’s for quite a while now. She’s a 14 year startup founder and 3x bootstrapper, currently the co-founder and CEO of eWebinar. Melissa is extremely generous about sharing her bootstrapped journey to $1M ARR and beyond on LinkedIn, through her ProfitLed Podcast, in the ‘your founder next door’ newsletter.
Melissa built a software company without an abundance of resources or friends in high places. Now she’s letting us in on exactly what didn’t work on their journey.
Previous to starting my first company, I had spent my career in enterprise sales. My first two companies sold products to big companies, which I grew through sheer will, cold calling, and lobby-conning (the subtle art of stalking the lobbies of conferences). I was a sales-led founder.
eWebinar, my current company, was different. With a starting price point of $99/month, it needed to be a product-led, customer-led, and marketing-led company. While founder-led sales got us off the ground, it became unsustainable after 9 months, my network and sanity exhausted.
Before eWebinar, I had no marketing experience, which turned out to be my biggest shortcoming in growing this company. Nobody on my team did either, so we did the best we could, talked to anyone who was willing to help, and educated ourselves on the internet.
We threw everything against the wall to see what stuck and, by the start of summer 2023, had brute forced our way to $1m ARR, 36 months after product launch. On our way there, we tried a bunch of go-to-market strategies that did not work. Here are the top 10.
1. Product Hunt
We spent two months prepping and a $7,500 consulting fee on our Product Hunt launch, got to the top 3 on a Tuesday (the best day for maximum exposure), and acquired one customer. It was one of the lowest ROI activities we've ever done. But, I learned a lot from this experience.
Product Hunt was great for refining product messaging, customer testimonials (in comments), and building awareness. Each day’s top 3 products are featured in the next day’s newsletter. If you care about raising capital, Ryan Hoover, the Founder of Product Hunt and Weekend Fund, keeps an eye on things.
It did nothing for revenue or user acquisition, and we got no actionable feedback. Most people only signed up to look at the product because we made it sound compelling and had pretty screenshots. The launch was hyped for a single day with little evergreen value. Being a B2B product with no free version, we were not a good fit for their audience, which was mostly product people and very early stage founders. Nifty consumer products do much better there.
Would I still have done it knowing what I know? Yes. But I'd spend two weeks and $0. Launching on Product Hunt was a good exercise because it forced us to think about our business and hone our value propositions early on. We didn’t set our expectations properly, but hopefully after reading this, you will – if this is something you’re planning to do.
And if you are, here is my Product Hunt Launch Checklist + Tips I can share from my experience of spending too much effort on it. Good luck!
Related: How June.so won Product Hunt, How Tango Became #1 Product of the Week
2. Digital marketing
We hired a number of agencies to "do digital marketing" for us, and ended up owning it ourselves.
I was told we needed an SEO audit of our site to optimize it for Google, lots of content on our blog, backlinks so we’d have authority, and ads to test product messaging. I had no idea what any of that meant. I just wanted someone else to do it.
In the first 18 months, we tried three full-service agencies, two backlink services, and two ad buyers. None of those relationships lasted more than a few months. The quality of their work was low and we didn’t see a return on investment, for two reasons:
We hired the most convenient choice because we didn’t know what to look for.
We hadn’t nailed our product messaging so there wasn’t a clear direction to follow.
I've unsuccessfully worked with over 20 digital marketers and firms in the last decade, I’m not proud of that and it has been incredibly frustrating. You may have experienced something similar.
The vicious cycle went something like this, using SEO as the prime example:
Hire seemingly good company for a minimum engagement of 3-6 months
Get a proposal of a new strategy as the old one was deemed to be bad
Technical and content audit + keyword research + new content
Receive basic and mediocre output with no measurable ROI
Realize company is not a good fit
Start over after spending $10k+
I finally realized what the problem was: We weren’t marketers so we couldn’t define success for someone else. We had no idea what needed to be done.
I learned that you can't pay someone else to take away your pain if you don't have a basic idea of how something works. That’s when we made a decision to learn key digital marketing practices from the ground up so we could own our strategy. It didn’t make sense to let someone else be responsible for our revenue.
We engaged Grow & Convert to teach us all things content writing and SEO, and followed Respona’s link building strategy and outreach. We vowed to never hire for a role we didn’t understand again. So did it work? Keep reading 👇
3. Paid ads
“Figure out a funnel where you can make $2 for every $1 in ad spend and you’re golden.” Says every marketer.
Sounds magical! But nobody talks about the elements that have to be in place for this utopian flywheel to be possible, and the amount of expertise, resources, and time required to experiment your way there.
Every ad buyer we talked to said we could start with a $500 monthly ad spend plus their retainer fee (~$1,500), so that’s what we did. We worked with two consultants, both came highly recommended. Over eight months, we tried Google, Facebook, and LinkedIn ads.
There were a number of problems. The first consultant only bought ads, but didn’t write copy. Which meant we had to give her copy to test without understanding how to write ad copy. The second consultant wrote copy, but we hadn’t done any customer research and didn’t know who our ideal customers were. Which meant he was shooting in the dark.
Our ads got very little engagement and no conversions for a variety of reasons beyond just copy.
The most important things we learned from this fruitless exercise:
Product: For your ad to be a scroll stopper, people need to know what you’re selling immediately. There's no room (literally) for education in the ad nor time to consume it while scrolling. If you are not in a mature, known product category, everyone will scroll right past you.
Messaging: Ad consultants are not there to help you figure out your value props, they’re there to help you test existing messaging and figure out the most compelling ways to communicate those value props to your ICPs.
Execution: The person who writes great copy, buys the ad, and optimizes the funnel could be three different people. Expect to spend money and time on each role, or to learn them yourself.
Cost: Ad costs are skyrocketing and ROI is dwindling because people do not want to be sold to, and since web traffic is up, conversion is low. You’re competing for eyeballs with big companies with massive budgets, which often doesn’t make sense for startups.
When we saw our ads weren’t converting, we thought it was only because we hadn’t figured out the messaging. I wish someone would’ve broken it down for us as to why we were not in a position to try paid ads, which would’ve saved us a lot of pain.
4. Writing mediocre content
We wanted to populate our blog and the internet with content, so we could look more established than we were, and appear in Google search.
As such, on top of the SEO agencies we hired to write content for us, we engaged cheap “PR companies” that charged a fixed fee for a guaranteed number of articles and invited contributors for guest posts.
The result was lots of low quality pieces of content. If even I couldn't finish reading them, how could I expect someone else to and convert from them? Nothing was converting.
We learned that writing content is easy, but writing GREAT content is HARD. The writers we worked with wrote for the sake of generating clicks, with no deep understanding of our business and customers. As a result, their content was basic and boring. Since they operated more like a factory and were rewarded by volume, there was no motivation for them to learn our business so that they could write more meaningfully and attract the advanced business users we cared most about.
Once we decided to own our content and SEO, we scrapped everything we’d done and started from scratch with a well-researched, defined content strategy to own our space.
Within a year, conversions from organic search to our blog went from 0 to 22%. Of the 131 bottom of the funnel keywords we targeted, 100 were in the top three.
Agencies and contractors can go from 1-to-2, but few can go from 0-to-1. It’s the job of the founding team to figure out how their startup should be positioned in the market, not the job of a third party. Until you know exactly how you want to show up in search and how you want to be perceived by customers, you can’t generate high quality content that converts. You certainly can’t give directions as to how to do that either.
Related: You need a better content strategy
5. Email outreach
Sales has always been my expertise and it was the only thing I’d done prior to starting my own company. Before eWebinar, direct outreach was the only way I knew how to find revenue before. I was really good at getting through gatekeepers and getting responses from decision makers.
Selling to my network and their referrals was how we got to first revenue; as that ran out, I knew we had to branch out to cold outreach. In the past, I had no problem selling high-ticket solutions ranging from $10-100k. I thought that selling a $100 solution would be much easier – I could not have been more wrong.
We hired a contractor from South Africa ($2,000 per month) who specialized in mass email outreach. He was versed in the whole works: scrounging for emails, validating them, warming up inboxes, messaging, automated outreach, etc. These are things I never learned how to do.
He worked with us for 11 months and the trial signups from his efforts were negligible. The problem wasn’t the approach, it was that this approach did not work for this price point of a product.
For $10k products, it’s normal for buyers to enter a sales cycle, schedule a call, hop on a demo, etc. (It’s also worth it for the seller to spend the time nurturing.) But $100 products are not bought in the same way. Low priced products are typically self-service where buyers do their own research and sign up for a trial.
The response rate to our email outreach was sub 2%, when I was used to 20% in the past with high priced solutions. The people who responded wanted a live demo which wasn’t something I was willing to offer given our price. It wouldn’t have made sense to enter into a sales cycle with prospects that required management and follow up. Our demo was available on-demand (delivered via eWebinar), but since our outreach was personal, they wanted the demo to be personal too, and so we couldn’t get interested parties to watch it.
Effort was high, response was low, and ROI was non-existent.
Related: Your guide to outbound automation feat. Thena and Clay
6. LinkedIn outreach
I started building an audience on LinkedIn by posting daily and saw how active people were on the platform. I thought outreach there might be a more effective way to get a response from someone than email, since LinkedIn offers a much more targeted approach to finding decision makers, especially within special purpose groups that you can join and reach out to members individually. So I decided to give it a shot.
I lasted almost four weeks before calling it off. I have been doing cold outreach since I was 20 years old and I never experienced people who were more angry than those on LinkedIn. People were offended by my messages. They’d curse and say how preposterous it was that I was misusing the platform to sell, and that I should be ashamed of myself. Emotionally, it was a shock.
I received a 24-hour block for self promotion and stopped what I was doing immediately because it was too valuable of a platform for me to build a business audience through my own content. I didn’t want to risk a permanent ban. There was no transparency with what happened so I can only assume that enough people reported me spamming them that I got a warning. Perhaps due to the low price point of our product, people took me less seriously.
I realized that I’d rather build a brand that people loved than the other way around. I’m glad I stopped because eventually, I got a lot of traction and engagement on my daily posts. I would have hated to be thought of as someone who violates someone’s private inbox.
7. Affiliates and partnerships
We spent $130,000 in 10 months on affiliate marketing and only attributed $500/month of revenue to it. This was the biggest financial mistake I’ve made in my career, the most expensive lesson I’ve ever learned.
The myth is that if you have a great product and offer a commission for people to promote it, they will and you’ll make a ton of money. Not so fast. While it was relatively easy to get people (influencers included) excited about our product, it was virtually impossible to get them to execute on a campaign.
I learned that having a great product is not enough to get someone else to sell it for you.
You need to be able to compensate affiliates enough to incentivize them, but not so much that it takes away your incentive to engage them.
You need to have a product that is mature enough such that selling it is not hard. Which means having a brand that is recognizable, ready-to-use marketing assets, and messaging that resonates with their audience right away. You can't rely on them to test the market for you. Affiliates are looking to make money fast, so the heavy lifting has to be done for them.
Once those elements are in place, be prepared to invest a lot of time into building relationships before they come to fruition. Which means you need enough runway to see positive ROI.
Our startup was too early to invest in this as a channel. Affiliates and partnerships is not a go-to-market strategy, but rather a growth strategy.
How did we spend so much? We hired an experienced partner manager to run this strategy for us, and we were too hopeful for too long.
Related: ProfitLed Podcast S2E16, Our $130k Mistake in Affiliate Marketing
8. Event sponsorships
An opportunity came up to sponsor an event for customer success managers, which was our ICP (ideal customer profile). It was a chance to get in front of 2,000 of them over three days. In-person events and manning booths was a big part of my life when I was in enterprise sales, so I knew it could work. But there was one big problem: the most basic sponsorship package was $10,000.
We were far from profitable at the time so spending money on sponsoring a conference initially did not make sense. Because we were a startup and had no intention of attending, the event host (large software company) discounted the sponsorship to $5,000, which included our 60-second promotional video on rotation throughout the event in various breakout rooms.
I suspected that it would be a waste of money given I wasn’t going to be there to network and actively sell, but since we were trying different go-to-market strategies, I wanted to give it my all and be sure.
To maximize our chances of exposure, we ran a contest for a $500 cash prize with a partner who was on-site. To enter the draw, all people had to do was sign up for an eWebinar demo. We got over 200 leads and none converted to a trial sign-up. We couldn’t even get the person who won the cash prize to get on a call with us.
In the world of high-ticket enterprise software, these types of sponsorships might make sense when you can make back the investment with a single sale. That’s when you can also justify the cost to attend in person. But for us, it was a doomed experiment from the start.
9. Newsletters
We paid $1,500 to sponsor a newsletter that went out to 100k people and got 298 clicks. That's a 0.3% click rate.
We ran a Black Friday deal with a partner that went out to 250,000 of their customers and got 18 trial sign ups. No one converted because their intention for signing up was to get the deal as opposed to solving a problem.
Lots of creators build newsletter audiences and offer advertising space. But after seeing such abysmal success rates, we would never again pay for a couple sentences in a newsletter. This strategy might make sense for higher priced products where a few sales can make up for the cost, but even then your pitch’s alignment with the overall content of the newsletter must be strong and relevant or you’ll never capture and convert readers.
10. Big website update
As our product grew, we outgrew the first version of our website. Our messaging wasn’t properly communicating our value props nor the features we had released over time. Design was simple and outdated, and our branding reflected a scrappy startup as opposed to the established, trustworthy startup we wanted to portray.
We hired a top branding agency to redo our site to be more of a Stripe and less of a new kid on the block and spent 7 months rewriting all the content based on customer interviews in hopes that our digital storefront would dazzle more prospects and increase conversion. After this grueling process was over, there was no lift. We did however, end up with a fresh new look and expandable website that will carry us into the next few years.
Related: ProfitLed Podcast S2E14, 10 Go-to-Market Strategies that Didn't Work, Anthony Pierri’s definitive SaaS homepage framework
A look back…
In hindsight, a lot of the lessons learned should have been obvious. But we didn’t have the experience and expertise to know – and that’s part of the process of growing a startup, figuring out what works and what doesn’t.
It’s easy to think that maybe we didn’t try hard or long enough on each of these strategies. I believe we gave every opportunity a fair shake. In the early days, our business had no credibility, product had little adoption, and we hadn’t built brand awareness. While it was important to be open-minded and optimistic, it was more important to recognize when it was time to change course and not waste resources on strategies that weren’t right for that moment in time.
The reality is the effectiveness of go-to-market strategies depends on many things: product, stage, messaging, time, investment, execution…what works as the business matures and changes may not work for a new startup, and vice versa.
We were resolved that most things we did in marketing wouldn’t work (very well, at least), but we did them anyway to find the few things that might. This is a philosophy we still believe.
There isn’t going to be one thing that significantly moves the needle and propels you into hockey stick growth – that is a myth for most startups.
The truth is many things you do will move the needle a little bit. It takes a lot of determination, trying, failing, decisions made, and lessons learned compounded over years.
Real, lasting growth takes time and hard work. Not hacks.
Follow along with Melissa’s bootstrapping journey: connect with her on LinkedIn, subscribe to her newsletter , follow her on Instagram, listen to her podcast (Apple | Spotify) or check out eWebinar.
 | A guest post by
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Wait, but what did work eventually?? So curious now!
so...uh...what worked?