Dec 23, 2020 · 18m · top-founders
Willco Breaks 10k Customers, $1m Revenue, $6m Valuation for End of Life Planning
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview with Nathan Latka, Willful co-founder and CEO Erin Bury details how the Canadian estate planning platform scaled past a $1M run rate, closed a $6M valuation seed round during the 2020 pandemic, and developed innovative life-event marketing and B2B partnership strategies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 38.8% of the talking time here. How this is scored →
Nathan as informed peer 6.4 Guest teaching 5.0 Guest disagreement 2.0 Nathan pushing back 3.6
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:15 Guest sets firm boundary on disclosing revenue
Erin directly halts Nathan's inquiry into full-year revenue numbers, explicitly stating she will not disclose that metric due to competitors.
Hardest push from Nathan ▶ 10:30 Host refuses deflection and probes run rateNathan refuses to let the revenue topic drop after Erin's refusal, immediately countering with a direct push on whether she has crossed the $1 million run-rate mark.
Biggest teaching moment ▶ 11:59 Guest refutes host's market comparisonErin rejects Nathan's assertion that Willful makes more revenue than Trust & Will, schooling him on US market scale and their distinct structural models.
Nathan holds their own ▶ 16:07 Host articulates affiliate EPC arbitrage mechanicsNathan displays sharp growth marketing expertise by unpacking the transition of EPC from niche affiliate marketing into mainstream tech customer acquisition.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Willful's Business Model and Life-Event Marketing Strategy | 5 | 5 | 1 | 3 | Nathan inquires about SaaS metrics, which prompts Erin to clarify that Willful operates as a transactional one-time payment model ($99-$149) rather than a recurring subscription. She explains how their revenue predictability relies on marketing around critical life milestones like childbirth or the passing of relatives. | |
| Securing Seed Funding and Valuation Dynamics Amid COVID-19 | 6 | 5 | 1 | 3 | Nathan digs into the mechanics of their mid-pandemic fundraise, SPVs, and how non-recurring revenue businesses justify seed valuations. Erin explains how framing the company as an e-commerce fintech rather than pure SaaS helped align expectations with angel investors. | |
| Content Marketing, SEO Mastery, and Strategic Partnerships | 7 | 4 | 3 | 6 | Nathan brings external SEO data from Ahrefs to evaluate Willful's organic search moat. When Erin explicitly declines to disclose exact historical revenue figures to protect competitive positioning, Nathan pushes past the deflection with a run-rate threshold question. | |
| Market Dynamics, Peer Collaboration, and Exit Ambitions | 6 | 7 | 4 | 4 | Nathan attempts to benchmark Willful against competitor Trust & Will by assuming Willful generated higher overall revenue. Erin corrects him regarding the vast size differential of the US market and peer collaboration, leading Nathan to backtrack and issue a correction. | |
| Shift in Affiliate Compensation to Earnings Per Click (EPC) | 8 | 4 | 1 | 2 | Erin shares that Willful has moved partner compensation from rev share to earnings per click (EPC). Nathan demonstrates deep domain knowledge by contextualizing how EPC migrated from internet affiliate forums into B2B SaaS and breaks down the risk arbitrage model. |
Statements from this episode (17)
Willful charges $99 to $149 one-time for estate documents with free updates
“So it's actually not a recurring product. It's more of a one-time transactional product. So you're paying us anywhere from 99 to 149 dollars for your documents, your will and power of attorney documents, and we offer free unlimited updates, which is a competit…”
Bury: About 60% of US and Canadian adults lack basic estate documents
“I feel like the sad truth is, and this is true in Canada as well as the U.S., people are woefully unprepared for their own passing, and about 60% of adults don't have just the simple legal documents”
Bury: Willful generated roughly a couple hundred thousand dollars in first year
“And you know, I think in the first year we probably did a couple 100,000 dollars of revenue.”
Bury: Willful closed a 1.1 million Canadian dollar seed round in May 2020
“1.1 million Canadian, which I think is like four dollars US.”
Bury: Willful closed its seed round at a 6 million dollar valuation
“No, we did it as a price round with a post-money valuation of six million.”
Bury: Willful raised early convertible debt primarily from Shopify executives
“We had done some convertible debt earlier on from mostly Shopify executives in Toronto.”
Bury: Willful drives growth through SEO, PR, and life-event partnerships
“You really start your search for estate planning and wills by hitting up Google, and so we've long known that PR, content marketing, and methodical SEO is going to be the way that we win, and the other big user acquisition channel for us is partnerships, so be…”
Bury: Willful partners with Wealthsimple and Parent Life Network for acquisition
“Some of them are Facebook groups, but the more official ones would be you know, Parent Life Network is a big one in Canada that that new moms are a part of, but even just other kind of fintechs that were partnered up with Wealthsimple and some of the other fol…”
Erin Bury: Willful has grown revenue 4x to 5x year-over-year
“We've seen like a four to five increase year over year”
Bury: Willful has broken a $1 million revenue run rate
“Yes, we've broken a million dollar run rate.”
Bury: Higher-ticket transactions or B2B can scale Willful to $10M run rate
“I don't know that we can get up to a ten million dollar runway rate with the only the current existing product because it is a bit of a lower price product. But as we start to look at things with more lucrative price points like estate administration tools, in…”
Bury: Willful offers family plans while Trust & Will uses subscriptions
“So for example, we have a family plan where you can buy multiple plans. They don't. So it's a way for them to validate that. They all have subscription. We don't.”
Erin Bury: Willful is targeting an acquisition exit rather than IPO
“I mean, obviously, there's a few paths for any company. There's IPO, exit, or staying profitable long-term, and I think we're very much on an exit path, and when we think about ideal acquirers, we want it to be somewhere where we want to work, right?”
Bury: Willful has 10k to 15k paying customers across 40k documents
“Yeah, I think I'd have to, again, check, but between 10 and 15,000 kind of paid customers to generate that 40,000 documents.”