The Ledger

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Insight
Chadha: Talent density rises astronomically after raising large capital rounds
“The talent density goes up astronomically after you've raised money, you know, with some big valuation numbers or big checks because people want to come and work. Your firm, and you are inviting your friends as well.”
Paroon Chadha Oct 9, 2022 ▶ 12:25 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Insight
Chadha: Six- and seven-figure secondary payouts transform company culture
“When you really find lots of folks around you in your team have made their first six-figure, seven-figure checks, and they work with you, it will completely change the culture. You don't have to worry. There's a proven culture of financial rewards, extraordina…”
Paroon Chadha Oct 9, 2022 ▶ 16:06 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Not checkable as stated
Chadha: OnBoard closed its fundraising cycle in 1.5 weeks
“For me, ah, the fundraising cycle was a very short one. It was just a week and a half.”
Paroon Chadha Oct 9, 2022 ▶ 17:17 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Insight
Chadha: Acquiring over 20% of ARR requires making executive hires first
“When you do an acquisition which is more than 20% of your ARR, it's gonna test you. You almost need to hire execs ahead of that transaction.”
Paroon Chadha Oct 9, 2022 ▶ 23:04 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Insight
Chadha: 200 customers in one vertical makes startups more investable
“First of all, stick with a niche. Niches will bring riches. Certainly, you know, I can you know, attest to that. If you have 200 customers in the same vertical, you're going to be more investable than actually being spread over lots of different verticals.”
Paroon Chadha Oct 9, 2022 ▶ 24:08 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Not checkable as stated
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.”
Paroon Chadha Aug 8, 2022 ▶ 5:42 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Insight
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.”
Paroon Chadha Aug 8, 2022 ▶ 12:59 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
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.”
Paroon Chadha Aug 8, 2022 ▶ 19:00 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Not checkable as stated
Shada: OnBoard was bootstrapped and profitable for 15 years
“Completely bootstrapped. Ran a profit for, believe it or not, 15 years.”
Paroon Chadha Aug 8, 2022 ▶ 19:59 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
Shada: He bought out all early partners to own 100% of OnBoard
“And eventually there came a time when there was no cap table. There was just a single cell. I owned all of it.”
Paroon Chadha Aug 8, 2022 ▶ 21:16 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Insight
Shada: Founders in evergreen spaces should build to own forever
“Investors will come and go if you find yourself in an evergreen space. Keep building like you're going to own this forever because you just might.”
Paroon Chadha Aug 8, 2022 ▶ 22:58 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Prediction Not checkable as stated
Passageways Closes 40% of Its Annual Business in November and December
“Believe it or not, between now and the end of the year, I'm gonna do 40% of the year's business.”
Paroon Chadha Nov 10, 2019 ▶ 13:38 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Chadha: OnBoard used debt to bootstrap to $15M ARR
“First actually really took on debt. To continue to bootstrap till we got to fifteen million dollars in ARR.”
Paroon Chadha Oct 9, 2022 ▶ 1:55 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Disclosure
Chadha: Ensemble generated $2M-$3M annually to fund OnBoard's growth
“Meanwhile, we continued down the path of taking the original product ensemble and making it into a cash cow, which funded the business two, three million dollars every year. That money was plowed back into growing the onboard business.”
Paroon Chadha Oct 9, 2022 ▶ 4:20 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Not checkable as stated
Chadha: OnBoard is currently growing revenue at a 50 percent rate
“At this time, you know, we are growing, you know, 50%, and we are actually really fast growing.”
Paroon Chadha Oct 9, 2022 ▶ 5:42 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Not checkable as stated
Chadha: OnBoard has 600 bank customers
“I have 600 banks as customers today.”
Paroon Chadha Oct 9, 2022 ▶ 7:37 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Disclosure
Chadha: OnBoard's first customer provided the loan for his co-founder buyout
“In my case, my first customer was also somebody who gave us infrastructure. We used their office. They also advised a lot on operations side. How do you get compliance certifications and such? And eventually they became my date partner. When I talked about buy…”
Paroon Chadha Oct 9, 2022 ▶ 10:00 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Insight
Chadha: Early customers are emotionally invested and act as an early board
“So you can get a lot out of your early customers. They are emotionally invested just like early employees. The question really comes down to what are you going to solve for with them? They're your early board, if you will.”
Paroon Chadha Oct 9, 2022 ▶ 10:25 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Disclosure
Chadha: OnBoard raised $5M primary plus secondary in first institutional round
“So the first check was actually only five million dollars on the balance sheet. I did take some you know, secondary off just to really kind of just ease the pain.”
Paroon Chadha Oct 9, 2022 ▶ 13:24 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Supported
Chadha: OnBoard raised $100 million in 2021
“We raised a hundred million last year.”
Paroon Chadha Oct 9, 2022 ▶ 15:14 Founder First PE Playbook: Growing from $24m Revenue Bootstrapper to $400m PE Valuation
Assertion Not checkable as stated
Shada: OnBoard has surpassed 3,000 customers
“We've grown past 3000 at this point.”
Paroon Chadha Aug 8, 2022 ▶ 2:31 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Not checkable as stated
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.”
Paroon Chadha Aug 8, 2022 ▶ 2:34 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Not checkable as stated
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.”
Paroon Chadha Aug 8, 2022 ▶ 3:56 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Not checkable as stated
Shada: eScribe had about 400 customers when acquired
“They had about 400 customers and change.”
Paroon Chadha Aug 8, 2022 ▶ 5:32 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
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.”
Paroon Chadha Aug 8, 2022 ▶ 7:33 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
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.”
Paroon Chadha Aug 8, 2022 ▶ 7:48 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
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.”
Paroon Chadha Aug 8, 2022 ▶ 8:17 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
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…”
Paroon Chadha Aug 8, 2022 ▶ 9:03 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Disclosure
Shada: Less than $50M of OnBoard's $100M raise was secondary
“Less than 50, yes.”
Paroon Chadha Aug 8, 2022 ▶ 9:30 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Prediction Not checkable as stated
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”
Paroon Chadha Aug 8, 2022 ▶ 18:24 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Partly supported
The US Supreme Court Uses Passageways for Its Board Management
“Now we have some of the largest customers in the world using our product, including some, you know very amazing non-profits Supreme Court in our country is using our product, some of the Fortune, 500 companies some of the biggest banks and hospitals using our …”
Paroon Chadha Nov 10, 2019 ▶ 5:01 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
Passageways Serves Over 1,000 Active Board Management Customers
“We're talking about more than a thousand customers at this point.”
Paroon Chadha Nov 10, 2019 ▶ 5:39 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Passageways Wins 25% to 30% of Qualified Sales Opportunities
“We win about, you know, 25, 30% of our, you know, opportunities.”
Paroon Chadha Nov 10, 2019 ▶ 7:09 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Passageways Holds $5 Million on Its Balance Sheet Post-Raise
“At this point, we are, you know, we have about five mil on the balance sheet.”
Paroon Chadha Nov 10, 2019 ▶ 8:28 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
Passageways Increased OnBoard ARR by 65% to 70% This Year
“We did grow 65, 70% this year. That's the ARR growth that we saw.”
Paroon Chadha Nov 10, 2019 ▶ 9:37 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
Passageways Maintains 3% Churn and 108% to 109% Net Retention
“Our churns you know, about three percent. Our dollar retention rate is, you know at this point, I think we are ending the year at about a 108 109%.”
Paroon Chadha Nov 10, 2019 ▶ 10:47 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
Passageways Operates With a 12-Month Payback Period on CAC
“We, you know, at this point you know, we're spending about a dollar to get you know, about a dollar in ARR.”
Paroon Chadha Nov 10, 2019 ▶ 11:54 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
OnBoard Drives Two-Thirds of Passageways' Total Annual Revenue
“Two thirds of the product of the revenue at this point is you know, projected to be board product by the end of the year. And one third is going to be an employee collaboration product.”
Paroon Chadha Nov 10, 2019 ▶ 13:01 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Financial Services Customers Generate 50% of Passageways' Total Revenue
“About 50% of my business is coming from the financial services industry.”
Paroon Chadha Nov 10, 2019 ▶ 13:48 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Supported
Shada: eScribe Was Largely Bootstrapped Prior to Acquisition
“Oh, it was actually really some angels, but it was bootstrapped. Yeah, largely bootstrapped.”
Paroon Chadha Aug 8, 2022 ▶ 11:41 How He Did $100m Secondary but also raised cash to buy a $5m+ ARR Competitor
Assertion Not checkable as stated
OnBoard Charges Between $5,000 and $60,000 Annually for Board Management
“You could get started for about 5000 dollars a year. It's per user but our larger customers about 50, 60,000 dollars a year.”
Paroon Chadha Nov 10, 2019 ▶ 3:40 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
OnBoard Averages $7,000 to $8,000 in Annual Contract Value
“The ACB is right around seven, 8000 dollars.”
Paroon Chadha Nov 10, 2019 ▶ 3:56 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Passageways Drives Two-Thirds of Acquisition Through Inbound Channels
“So most of it is, you know about two thirds of it is inbound and one third is outbound.”
Paroon Chadha Nov 10, 2019 ▶ 5:52 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Passageways Employs 100 People, Including 15 Sales Development Reps
“We are right around a hundred people at this point, and about 15 SDRs.”
Paroon Chadha Nov 10, 2019 ▶ 6:19 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Disclosure
Passageways Maintains a 1:1 Ratio of SDRs to Account Executives
“So we have almost a one to one ratio on the SDR to AEs.”
Paroon Chadha Nov 10, 2019 ▶ 6:34 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
350 Enterprise Customers Still Use Passageways' 2003 Legacy Product
“We launched that in, you know, back in 2003. And we do have three 50 customers, enterprise customers using that product.”
Paroon Chadha Nov 10, 2019 ▶ 10:28 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
Assertion Not checkable as stated
Passageways Still Uses QuickBooks for Billing at 1,000-Customer Scale
“We're still using QuickBooks.”
Paroon Chadha Nov 10, 2019 ▶ 14:50 1569 Why 1000+ Boarddecks Get Manged Using This $7m ARR Tool
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