Jul 16, 2019 · 26m · saastr
"Our best and worst marketing experiments" Lucidchart Co-Founder and CEO Karl Sun
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Lucid Software CEO Karl Sun details Lucidchart's most impactful and disastrous marketing experiments, demonstrating how a culture of disciplined trial and error, value transparency, and creative risk-taking fueled the company's rapid growth and brand evolution.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:45 Karl admitting internal dissent over credit cards
In a monologue format with zero interpersonal combativeness, Karl describes his own strong internal skepticism and opposition to requiring credit cards before seeing the data.
Hardest push from Jason ▶ 19:40 Pulling the Walter campaignBecause this is a solo talk without an active host, the nearest analog is the company shutting down the crowdsourced Walter experiment within days due to internet misuse.
Biggest teaching moment ▶ 6:00 Explaining commitment ladders in trial conversionKarl educates the audience on moving users from zero to partial commitment rather than jumping from free to full paid conversion.
Jason holds their own ▶ 24:30 Warning against trusting raw data or gut instinct blindlyKarl presents expert domain insights to the audience, synthesizing how neither uncritical reliance on data nor executive gut instinct alone suffices for growth.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Company Growth and Structuring a Culture of Experimentation | 0 | 0 | 0 | 0 | This is a solo presentation monologue by Karl Sun without host interaction. He outlines company background, growth metrics, and setting up an experimental growth team. | |
| Increasing Conversion by Requiring Credit Cards on Free Trials | 0 | 0 | 0 | 0 | Monologue segment detailing the counterintuitive experiment of requiring credit cards on free trials. There is no host involvement or disagreement. | |
| Re-evaluating the Freemium Anchor to Emphasize Product Value | 0 | 0 | 0 | 0 | Karl Sun describes pricing redesigns and homepage overhaul iterations. As a presentation monologue, all interaction metrics remain at zero. | |
| Expanding Brand Reach with the Songtacular Flowdown Campaign | 0 | 0 | 0 | 0 | Karl shares the Songtacular Flowdown creative experiment, accompanied by audio playback. No host dynamic is present. | |
| Engaging Audiences with Pop Culture and Infographic Flowcharts | 0 | 0 | 0 | 0 | Karl humorously recounts the failed crowdsourced Walter diagram campaign and pop culture flowcharts. No host participation occurs. | |
| Lucidchart Explains the Internet Viral Doggo Video Series | 0 | 0 | 0 | 0 | Karl explains how an engineer's meme pitch became the viral Lucidchart Explains the Internet campaign. Delivered purely as a solo keynote. | |
| Core Principles and Key Takeaways on Business Experimentation | 0 | 0 | 0 | 0 | Karl concludes his solo keynote by summarizing four key takeaways on business experimentation and company culture. |
Statements from this episode (13)
Lucid Software reaches 96% of Fortune 500 and adds 700K monthly users
“We have over 500 employees now. Over fifteen million users spread across over a 180 countries, and we're represented in 96% of the Fortune 500 companies and adding about 700,000 users every month.”
Lucid Software's growth team generated $1M incremental ARR in its first quarter
“So, when we started when we started the growth team, we had this goal that, ah, we, you know, our target was if they can be successful, that would mean they would contribute like a million dollars in incremental revenue, ARR, over the course of that first year…”
Requiring credit cards for free trials generated $500K incremental ARR for Lucidchart
“These changes ultimately on, on the pricing page ended up back in the day for us, Contributing about 500,000 dollars of incremental revenue in just 12 months, which was a huge win for us back at the time. And overall, they increased payments by 25%, which is o…”
Karl Sun initially opposed requiring credit cards for Lucidchart's free trials
“I was actually one of those people. I was against this approach. I said, well, let's try it, but I don't like it.”
Emphasizing free plans increased Lucidchart registrations but hurt downstream paid conversions
“And our thought, obviously, was that, you know, free would lower the barrier for people to enter, and it's true that it increased a lot of registrations, right? But what happened is we brought in a lot of interest, but they were, because they were anchored on …”
Replacing 'start free trial' with 'try or buy' improved Lucidchart's lead quality
“And instead of saying, start a free trial, We've now saying, you know, try or buy, and so that's a actually meaningful difference, like just de-emphasizing that idea of free. And so what we found is, you know, obviously we've lost some traffic, lost some regis…”
Desaturated org charts with grayed-out faces converted best on Lucidchart's homepage
“This org chart was the most effective, and not only was the org chart more effective, but we realized that when you put people's faces in pictures, it resonated more with people, and even furthermore, it worked best when these faces were sort of grayed out or …”
Lucidchart's viral song flowchart campaign originated in a summer hackathon
“Out of a summer hackathon, there was this idea for what we call the songtacular flowdown, where we would take popular songs and use it to display the ease of use and functionality of our product.”
Lucidchart's viral pop culture flowcharts ultimately failed to communicate core product utility
“We realized it actually didn't do a great job of introducing you to the product, even less so than the song ones, and telling you how to use our product or what it would be useful for.”
Lucidchart's original doggo meme video received 33 million organic views in days
“Within a couple of days, it got thirty-three million views, and we had not done a single thing to push it.”
Lucidchart's 'Explains the Internet' marketing campaign surpassed 280 million total views
“This campaign is called Lucidchart Explains the Internet and it now has over two hundred and eighty million views.”
Adweek named Lucidchart's series the only ad campaign that mattered in 2018
“And actually, it was recognized by Adweek last year as, quote, the only ad campaign that truly mattered in 2018.”
Blindly trusting conversion data would have trapped Lucidchart with a poor homepage
“If we had trusted, just purely trusted the data on all of those homepage experiments, We would still be stuck with that really crappy homepage as opposed to something that I think resonates more as we evolve as a company.”