Aug 8, 2022 · 26m · top-founders
How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
OnBoard founder and CEO Parun Shada breaks down how the board governance software company scaled past $35 million ARR through 15 years of bootstrapped discipline, strategic partner buyouts, an eight-figure divestiture, and the acquisition of public-sector competitor eScribe.
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 28.8% of the talking time here. How this is scored →
Nathan as informed peer 4.4 Guest teaching 1.9 Guest disagreement 1.3 Nathan pushing back 3.1
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 9:02 Parun rejects secondary round premise
Parun directly interrupts and corrects Nathan's characterization of their hundred million dollar financing as pure secondary liquidity.
Hardest push from Nathan ▶ 23:21 Nathan calls out Parun's equity dodgeNathan refuses to accept Parun's vague non-answer about his personal equity stake, explicitly highlighting that Parun dodged the question.
Biggest teaching moment ▶ 9:02 Parun educates on round allocationParun educates Nathan on how the capital was allocated across primary growth balance sheet, acquisition cash for eScribe, and secondary liquidity.
Nathan holds their own ▶ 18:42 Nathan models $30M+ run rate from past metricsNathan combines historical customer numbers, ACVs, and the newly disclosed eScribe acquisition data to accurately calculate Parun's ARR run rate.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Parun Shada and the Board Meeting Challenge | 5 | 1 | 1 | 2 | Nathan calculates eScribe's likely ARR based on seat count and ACVs, while Parun cooperatively explains the strategic rationale and customer acquisition metrics. | |
| Divesting Ensemble to Solidify Focus on Governance | 4 | 1 | 1 | 4 | When Parun cites NDA limitations regarding the exact revenue from divesting Ensemble, Nathan swiftly reframes the question to focus on percentage of total company revenue. | |
| Deconstructing the $100M Capital Round and Valuation | 5 | 4 | 2 | 4 | Parun corrects Nathan's assumption that the $100M round was entirely secondary, explaining it combined primary, secondary, and M&A capital. Nathan then drills into valuation multiples. | |
| M&A Rollover Structures and Expanding Go-To-Market Teams | 4 | 2 | 1 | 3 | Nathan presses on the rollover equity versus cash buyout structure for bootstrapped targets, and Parun breaks down his general rule of thumb and go-to-market hiring. | |
| Sponsor Advertisement: Collide Device Security | 6 | 2 | 1 | 3 | Nathan constructs a synthesized deal valuation model based on previous clues, and calculates the combined ARR trajectory toward thirty-five million dollars. | |
| Fifteen Years Bootstrapped and Buying Out Early Partners | 3 | 2 | 1 | 1 | Parun narrates the unique cap table history of using debt and cash flow to buy out two early partners to reach single-cell ownership before taking PE capital. | |
| Two Decades of Leadership and Long-Term Ownership | 4 | 1 | 2 | 5 | When Nathan asks Parun for his current personal equity percentage, Parun attempts to hedge, leading Nathan to playfully call him out for dodging the question. |
Statements from this episode (17)
Shada: OnBoard adds 80 to 100 new customers monthly
“And we are adding about, you know I'd say about 80 to a hundred customers a month. That's the clip that we are operating at.”
Shada: eScribe's pre-acquisition ACV was around $20K to $25K
“They are actually higher. So if you think of a city council, there's often, you know, a much bigger number of people involved, some more subscribers their you know, average contract you know, pre-transaction was right around 20, 25.”
Shada: eScribe was doing $5M to $10M in revenue at acquisition
“Yeah, I know. I would say, you know, just short of that, but yeah, that was sort of the revenue range. You know, they were in the five to ten million range, but I don't know the exact specific number this time, but yeah.”
Shada: OnBoard sold Ensemble for an eight-figure sum
“No, I think we sold in November. I was a good time. Actually, it was actually, it was certainly, you know you know, it was eight figures. It was actually a good transaction.”
Shada: Ensemble generated under $10M ARR prior to sale
“Ensemble had you know, I don't know if I'm you know, if I should disclose the revenue, but it was actually, the range was less than ten million.”
Shada: Ensemble made up roughly 25% of OnBoard's revenue
“Ensemble was, you know, about, I would say, 25, 25% of our revenue, and when we swapped out Ensemble for Eastcry, we are actually, you know, further ahead.”
Shada: OnBoard's $100M round combined primary capital and secondary liquidity
“It was not a hundred million secondary. It was actually primary and secondary combined. It was actually a hundred million dollar round.
Some of that capital was used for this acquisition.
Some of that capital was secondary.
Some of that capital actually wen…”
Shada: eScribe Was Largely Bootstrapped Prior to Acquisition
“Oh, it was actually really some angels, but it was bootstrapped. Yeah, largely bootstrapped.”
Shada: Bootstrapped founders should cash out half their equity in M&A deals
“A good rule of thumb is, you know, you take half off and then, you know, in the new combined entity, you are back on the schedule to get some more options. So you are actually back in the Western schedule.”
Shada: OnBoard targets close to 50% growth rate for the year
“So we'll, we'll actually really end
you know, close to 50% growth rate for the year.
If the rest of the plan year checks out”
Shada: OnBoard is past $30M run rate, targeting up to $37M
“That is accurate.
And, you know, ending the year you know, of course with a few big months, end of the year accurately, you know, we could get to numbers that are higher than, you know, closer towards 35, 37.”
Shada: OnBoard was bootstrapped and profitable for 15 years
“Completely bootstrapped. Ran a profit for, believe it or not, 15 years.”