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Jul 21, 2020 · 28m · startups-for-the-rest-of-us

Episode 506 | Shutting Down and Starting Up with Derrick Reimer

Derrick Reimer · 13m spoken Rob Walling · 13m spoken
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In this episode of Startups for the Rest of Us, host Rob Walling speaks with Drip co-founder Derrick Reimer about the valuable lessons learned from sunsetting Level and StaticKit. Derrick outlines how these hard-earned insights shaped his structured validation process, positioning strategy, and upcoming launch for his new scheduling platform, MightyCal.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Rob holds 50.1% of the talking time here. How this is scored →

Rob as informed peer 6.0 Guest teaching 1.3 Guest disagreement 0.0 Rob pushing back 0.5
05100:0010:0020:000:59–6:32 · Rob as informed peer 6/10 TinySeed Fund Two Investor Announcement Rob Walling introduces the episode and recaps their shared history co-founding Drip before diving into Derrick's ambitious project Level. Walling highlights the high switching costs and mobile app moats of Slack, which Reimer corroborates with lessons learned using The Mom Test methodology.6:32–12:31 · Rob as informed peer 6/10 Exploring StaticKit and Jamstack Monetization Realities Derrick explains how StaticKit emerged as a therapeutic developer tool in the nascent Jamstack ecosystem, only to hit monetization walls without enterprise sales. Rob validates this dynamic by comparing Jamstack's wave to early WordPress and discussing when founders should pivot rather than throw good time after bad.12:31–16:53 · Rob as informed peer 7/10 Ideation Process and Discovery for MightyCal Derrick outlines his structured rubric for evaluating SaaS ideas based on tools used at Drip, landing on scheduling software. Rob actively contributes product ideas like overlaying calendars and draws analogies to Superhuman and modern email clients innovating on mature categories.16:54–22:10 · Rob as informed peer 8/10 Analyzing the Scheduling Market, Pricing, and Growth Rob breaks down SaaS expansion revenue, per-seat pricing models, and the strategic advantages of competing in massive multi-million dollar spaces versus tight niches for ambitious founders. Derrick acknowledges the positioning risks and apathy barrier among current Calendly users.22:12–26:53 · Rob as informed peer 6/10 Customer Personas and Built-In Product Virality The conversation examines target avatars and native viral feedback loops in booking links. Rob and Derrick reminisce on similar 'Powered by Drip' viral mechanisms that propelled their previous startup.26:54–27:57 · Rob as informed peer 3/10 Dogfooding MightyCal and Preparing Early Access Rollout In a brief wrap-up, Derrick shares that his development burndown chart is at 96% and prepares for private early access rollouts. Rob jokes about holding him accountable and shares Derrick's project links.0:59–6:32 · Guest teaching 2/10 TinySeed Fund Two Investor Announcement Rob Walling introduces the episode and recaps their shared history co-founding Drip before diving into Derrick's ambitious project Level. Walling highlights the high switching costs and mobile app moats of Slack, which Reimer corroborates with lessons learned using The Mom Test methodology.6:32–12:31 · Guest teaching 3/10 Exploring StaticKit and Jamstack Monetization Realities Derrick explains how StaticKit emerged as a therapeutic developer tool in the nascent Jamstack ecosystem, only to hit monetization walls without enterprise sales. Rob validates this dynamic by comparing Jamstack's wave to early WordPress and discussing when founders should pivot rather than throw good time after bad.12:31–16:53 · Guest teaching 1/10 Ideation Process and Discovery for MightyCal Derrick outlines his structured rubric for evaluating SaaS ideas based on tools used at Drip, landing on scheduling software. Rob actively contributes product ideas like overlaying calendars and draws analogies to Superhuman and modern email clients innovating on mature categories.16:54–22:10 · Guest teaching 1/10 Analyzing the Scheduling Market, Pricing, and Growth Rob breaks down SaaS expansion revenue, per-seat pricing models, and the strategic advantages of competing in massive multi-million dollar spaces versus tight niches for ambitious founders. Derrick acknowledges the positioning risks and apathy barrier among current Calendly users.22:12–26:53 · Guest teaching 1/10 Customer Personas and Built-In Product Virality The conversation examines target avatars and native viral feedback loops in booking links. Rob and Derrick reminisce on similar 'Powered by Drip' viral mechanisms that propelled their previous startup.26:54–27:57 · Guest teaching 0/10 Dogfooding MightyCal and Preparing Early Access Rollout In a brief wrap-up, Derrick shares that his development burndown chart is at 96% and prepares for private early access rollouts. Rob jokes about holding him accountable and shares Derrick's project links.0:59–6:32 · Guest disagreement 0/10 TinySeed Fund Two Investor Announcement Rob Walling introduces the episode and recaps their shared history co-founding Drip before diving into Derrick's ambitious project Level. Walling highlights the high switching costs and mobile app moats of Slack, which Reimer corroborates with lessons learned using The Mom Test methodology.6:32–12:31 · Guest disagreement 0/10 Exploring StaticKit and Jamstack Monetization Realities Derrick explains how StaticKit emerged as a therapeutic developer tool in the nascent Jamstack ecosystem, only to hit monetization walls without enterprise sales. Rob validates this dynamic by comparing Jamstack's wave to early WordPress and discussing when founders should pivot rather than throw good time after bad.12:31–16:53 · Guest disagreement 0/10 Ideation Process and Discovery for MightyCal Derrick outlines his structured rubric for evaluating SaaS ideas based on tools used at Drip, landing on scheduling software. Rob actively contributes product ideas like overlaying calendars and draws analogies to Superhuman and modern email clients innovating on mature categories.16:54–22:10 · Guest disagreement 0/10 Analyzing the Scheduling Market, Pricing, and Growth Rob breaks down SaaS expansion revenue, per-seat pricing models, and the strategic advantages of competing in massive multi-million dollar spaces versus tight niches for ambitious founders. Derrick acknowledges the positioning risks and apathy barrier among current Calendly users.22:12–26:53 · Guest disagreement 0/10 Customer Personas and Built-In Product Virality The conversation examines target avatars and native viral feedback loops in booking links. Rob and Derrick reminisce on similar 'Powered by Drip' viral mechanisms that propelled their previous startup.26:54–27:57 · Guest disagreement 0/10 Dogfooding MightyCal and Preparing Early Access Rollout In a brief wrap-up, Derrick shares that his development burndown chart is at 96% and prepares for private early access rollouts. Rob jokes about holding him accountable and shares Derrick's project links.0:59–6:32 · Rob pushing back 1/10 TinySeed Fund Two Investor Announcement Rob Walling introduces the episode and recaps their shared history co-founding Drip before diving into Derrick's ambitious project Level. Walling highlights the high switching costs and mobile app moats of Slack, which Reimer corroborates with lessons learned using The Mom Test methodology.6:32–12:31 · Rob pushing back 0/10 Exploring StaticKit and Jamstack Monetization Realities Derrick explains how StaticKit emerged as a therapeutic developer tool in the nascent Jamstack ecosystem, only to hit monetization walls without enterprise sales. Rob validates this dynamic by comparing Jamstack's wave to early WordPress and discussing when founders should pivot rather than throw good time after bad.12:31–16:53 · Rob pushing back 1/10 Ideation Process and Discovery for MightyCal Derrick outlines his structured rubric for evaluating SaaS ideas based on tools used at Drip, landing on scheduling software. Rob actively contributes product ideas like overlaying calendars and draws analogies to Superhuman and modern email clients innovating on mature categories.16:54–22:10 · Rob pushing back 1/10 Analyzing the Scheduling Market, Pricing, and Growth Rob breaks down SaaS expansion revenue, per-seat pricing models, and the strategic advantages of competing in massive multi-million dollar spaces versus tight niches for ambitious founders. Derrick acknowledges the positioning risks and apathy barrier among current Calendly users.22:12–26:53 · Rob pushing back 0/10 Customer Personas and Built-In Product Virality The conversation examines target avatars and native viral feedback loops in booking links. Rob and Derrick reminisce on similar 'Powered by Drip' viral mechanisms that propelled their previous startup.26:54–27:57 · Rob pushing back 0/10 Dogfooding MightyCal and Preparing Early Access Rollout In a brief wrap-up, Derrick shares that his development burndown chart is at 96% and prepares for private early access rollouts. Rob jokes about holding him accountable and shares Derrick's project links.

speaking balance: gold is Rob, purple is the guest (3 minute bins)

0:00 · Rob 97.7% · guest 2.3%0:00 · Rob 97.7% · guest 2.3%3:00 · Rob 23.6% · guest 76.4%3:00 · Rob 23.6% · guest 76.4%6:00 · Rob 32.6% · guest 67.4%6:00 · Rob 32.6% · guest 67.4%9:00 · Rob 25.6% · guest 74.4%9:00 · Rob 25.6% · guest 74.4%12:00 · Rob 37.2% · guest 62.8%12:00 · Rob 37.2% · guest 62.8%15:00 · Rob 52.9% · guest 47.1%15:00 · Rob 52.9% · guest 47.1%18:00 · Rob 58.3% · guest 41.7%18:00 · Rob 58.3% · guest 41.7%21:00 · Rob 65.8% · guest 34.2%21:00 · Rob 65.8% · guest 34.2%24:00 · Rob 43.9% · guest 56.1%24:00 · Rob 43.9% · guest 56.1%27:00 · Rob 82.7% · guest 17.3%27:00 · Rob 82.7% · guest 17.3%
Sharpest disagreement ▶ 11:08 Derrick balancing gut instinct versus persistent effort

In a highly collaborative and friendly episode with virtually zero hostility, Derrick reflects on the difficult tension between dogged persistence and pivoting based on harsh market feedback.

 Hardest push from Rob ▶ 19:08 Rob probing the risk of market failure

Rob challenges Derrick to confront the downside scenario directly, asking why MightyCal might fail if they look back in a year.

 Biggest teaching moment ▶ 9:30 Derrick detailing Jamstack monetization traps

Derrick explains why Jamstack and developer form backends struggle with self-serve monetization, outlining why VC-funded competitors rely on enterprise tiers to generate revenue.

 Rob holds their own ▶ 21:00 Rob explaining big market economics vs niche stair-stepping

Rob provides an authoritative breakdown of when founders should choose large competitive markets over tight niche categories based on revenue ambitions.
the scores for every segment, with the reasoning behind each
ChapterTopicRob as informed peerGuest teachingGuest disagreementRob pushing backWhy
TinySeed Fund Two Investor Announcement 6201 Rob Walling introduces the episode and recaps their shared history co-founding Drip before diving into Derrick's ambitious project Level. Walling highlights the high switching costs and mobile app moats of Slack, which Reimer corroborates with lessons learned using The Mom Test methodology.
Exploring StaticKit and Jamstack Monetization Realities 6300 Derrick explains how StaticKit emerged as a therapeutic developer tool in the nascent Jamstack ecosystem, only to hit monetization walls without enterprise sales. Rob validates this dynamic by comparing Jamstack's wave to early WordPress and discussing when founders should pivot rather than throw good time after bad.
Ideation Process and Discovery for MightyCal 7101 Derrick outlines his structured rubric for evaluating SaaS ideas based on tools used at Drip, landing on scheduling software. Rob actively contributes product ideas like overlaying calendars and draws analogies to Superhuman and modern email clients innovating on mature categories.
Analyzing the Scheduling Market, Pricing, and Growth 8101 Rob breaks down SaaS expansion revenue, per-seat pricing models, and the strategic advantages of competing in massive multi-million dollar spaces versus tight niches for ambitious founders. Derrick acknowledges the positioning risks and apathy barrier among current Calendly users.
Customer Personas and Built-In Product Virality 6100 The conversation examines target avatars and native viral feedback loops in booking links. Rob and Derrick reminisce on similar 'Powered by Drip' viral mechanisms that propelled their previous startup.
Dogfooding MightyCal and Preparing Early Access Rollout 3000 In a brief wrap-up, Derrick shares that his development burndown chart is at 96% and prepares for private early access rollouts. Rob jokes about holding him accountable and shares Derrick's project links.

Statements from this episode (8)

Disclosure
Rob Walling: TinySeed has funded 23 companies and is raising Fund II
“And today we have funded 23 companies with our first fund, and now we are raising that second fund.”
Rob Walling Jul 21, 2020 ▶ 1:12
Insight
Reimer: Huge gap between employees hating Slack and securing approval to switch
“A big, big learning that, that smacked me right in the face once I Attempted to, ah, to kind of launch it after building it for about nine months was just the wide chasm between people's recognition that their communication patterns are not healthy and that a …”
Derrick Reimer Jul 21, 2020 ▶ 4:16
Insight
Reimer: Jamstack developer platforms require large free tiers and enterprise sales
“Some of the large hosting platforms like Netlify, like Vercel have, you know, kind of demonstrated that, you know, you need a large free tier at the bottom to kind of service the folks who are just playing with stuff and then ultimately like make your money se…”
Derrick Reimer Jul 21, 2020 ▶ 10:39
Disclosure
Reimer: Scheduling tools appeal due to single-player utility and fast MVP builds
“The opposite of level, like, people can use this in single player mode, which is very attractive to me, and you know, it's something that I could build the kernel of decently quick, and so that kind of checked those boxes right away”
Derrick Reimer Jul 21, 2020 ▶ 15:05
Opinion
Reimer: Main risk against Calendly is user apathy with 'good enough' software
“I think a big risk is getting the positioning right with people, like unlocking the positioning of people who really care about a more powerful, better curated experience. I did sense among some folks kind of a, an apathy or like a, yeah, Calendly's fine. It's…”
Derrick Reimer Jul 21, 2020 ▶ 19:17
Assertion Supported
Walling: Derrick Reimer sold CodeTree for $128K
“Code tree, which is an app we've talked about in the past that you sold for, you know, what, a hundred and 128 K several years ago.”
Rob Walling Jul 21, 2020 ▶ 20:29
Opinion
Reimer: Scheduling incumbents have overly broad positioning
“What I see a lot right now among others in this space is extremely broad positioning. And I think there's an opportunity here to kind of speak a little more directly to some specific pains. And be the de facto tool for that group.”
Derrick Reimer Jul 21, 2020 ▶ 24:43
Assertion Not checkable as stated
Walling: 'Powered By' badges drove growth for Drip and Calendly
“You know that that was a driver in the Drip days, because we had the widget, the Powered by Drip. You know that that was a driver in Calendly's growth.”
Rob Walling Jul 21, 2020 ▶ 25:35
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