Oct 24, 2024 · 23m · top-founders
Bending Spoons just bought his company for $100,000,000+ with Issuu CEO Joe Hyrkin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
At SaaS Open, former Issuu CEO Joe Hyrkin and Nathan Latka discuss Issuu's nine-figure, all-cash acquisition by Bending Spoons, sharing vital lessons on scaling ARR, managing predatory venture debt, and executing M&A.
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 27.9% of the talking time here. How this is scored →
Nathan as informed peer 6.2 Guest teaching 4.6 Guest disagreement 3.2 Nathan pushing back 4.0
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 3:51 Pushback on 6x multiple assumption
Joe firmly cuts off Nathan's proposed 4-6x revenue multiple range, stating bluntly that non-AI SaaS companies cannot fetch north of 5x in the current market.
Hardest push from Nathan ▶ 14:28 Refusal to let 12 percent interest mask predatory lendingNathan interrupts to emphasize the interest rate on the debt deal, challenging the common misconception that predatory lending only happens at exorbitant 40 percent rates.
Biggest teaching moment ▶ 21:24 Educating founders on the illusion of multiple strategic acquirersJoe educates the audience and host on M&A dynamics, dispelling the myth that dozens of strategics will bid against each other by pointing out that most drop out due to internal distractions.
Nathan holds their own ▶ 17:02 Calculating warrant drag on nine-figure exitsNathan breaks down the compounding dollar cost of warrant penalties on a 100M+ exit, showing mastery of venture debt mechanics to pitch cleaner financing alternatives.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Nathan Welcomes Former Issuu CEO Joe Hyrkin | 6 | 5 | 4 | 5 | Nathan presses Joe hard for specific deal terms and valuation multiples right away. Joe playfully pushes back against giving exact figures before educating Nathan on current valuation multiples, noting that nobody outside AI gets north of a 5x multiple today. | |
| Issuu Product Overview and Early Scaling Timeline | 5 | 3 | 2 | 2 | Nathan presents Issuu's historical revenue graph on screen while Joe walks through the product pivot from PDF hosting to B2B marketing collateral. The tone is collaborative and focused on narrative context. | |
| Executive Transition and Flipping Issuu to the US | 6 | 4 | 3 | 4 | Nathan digs into the cap table, funding history, and Joe's executive compensation package upon taking over. Joe explains why replacing a founder-CEO cleanly before hiring a replacement avoids loyalty confusion and shares how flipping to a US corporate structure worked. | |
| Navigating Predatory Debt Covenants and Eastward Refinancing | 7 | 6 | 4 | 5 | Joe details his experience with a predatory debt lender who used a minor revenue covenant miss to demand aggressive warrant penalties. Nathan jumps in to define debt compliance covenants and explains why predatory behavior exists even at seemingly reasonable 12 percent interest rates. | |
| Managing Cost of Capital and Eliminating Distractions | 7 | 5 | 3 | 4 | Nathan breaks down the financial hit of warrant dilution on a nine-figure exit, pitching alternative structures. Joe provides valuable advice on M&A realities, explaining why prospective strategic bidders like Canva or Adobe often fall away compared to decisive PE buyers like Bending Spoons. |
Statements from this episode (15)
Hyrkin: Bending Spoons buys $25M-$200M ARR companies to hold long-term
“What they're doing is they're buying companies that have, ah, some pretty good scale kind of revenue in the 25 to two hundred million dollar range, profitable or close to it, and then they go run them They buy to own. It's not a P firm.”
Hyrkin: Issuu sold for nine figures at $30M+ revenue
“As a company, we're doing just north of thirty million in revenue. Profitable. Not, not very profitable, but sort of barely profitable. And we sold the company for nine figures.”
Hyrkin: Non-AI SaaS companies cannot get revenue multiples above 5x
“Not six. I mean unless you're AI right now, you're not getting north of five.”
Hyrkin: Issuu would have fetched 2x-3x higher price in 2022 market
“Given the stage of where issue was when we sold it in July, if we had sold it two years prior in 22, we would have gotten two to three X what we got.”
Hyrkin: Issuu had 1M annual free users and 65k paying customers
“We had a million free customers a year, marketers, content creators 65,000 of them paying issue.”
Hyrkin: Issuu acquisition by Bending Spoons was all cash without earnouts
“Well, it was all cash, no earnouts.”
Hyrkin: Received significantly higher equity than typical hired CEOs at Issuu
“I got I got a nice compact, I'm not gonna give you the specifics, but I got a high, a much higher percent of the company than normally when you bring in a CEO.”
Hyrkin: Raising equity in 2021 would have required a $1B exit
“So instead of raising, we would have had to raise thirty million on a two hundred and fifty million dollar valuation, which meant that For everyone to feel successful, we would have had to have a billion dollar exit, which may have happened, but I wanted to ma…”
Hyrkin: Issuu took $20M of debt in 2021 despite $31M announcement
“We, ah, took on twenty million dollars of debt, actually, and had access to another 10. So it was announced as 31, but it was really 20.”
Hyrkin: Issuu missed a quarterly debt covenant by $150K on $7M
“However, about a year into it, we missed our revenue covenant by a footfall. So on a seven million dollar quarter, we missed by about a 150 K.”
Hyrkin: Debt lender demanded 1% equity monthly and $1M penalty
“And this firm continued to negotiate with us after we had verbally agreed and kept squeezing and adding in more and more and more and more terms to the point where they started to demand they wanted at one point, an additional point in the company for each mon…”
Hyrkin: Bending Spoons did not retrade price terms during Issuu acquisition
“One of the great things about working with Bending Spoons, they didn't retrade with us. I don't think they've retraded with others, meaning changed the price. Terms were the terms.”
Hyrkin: Issuu had deep acquisition discussions with Canva and Adobe
“We were, we had really deep conversations with Canva and Adobe.”
Hyrkin: Most acquisitions ultimately come down to only one to three buyers
“Most companies, when they get acquired, there's one to three that really come to the table. So, don't be disappointed if the 20 folks that you thought were gonna buy you, that you thought were gonna keep Raising the price and quadrupling it if that doesn't hap…”