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Dec 8, 2019 · 18m · top-founders

1597 How He Used a Search Fund To Build $7m ARR Company, Low Risk

Will Bressman · 9m spoken Nathan Latka · 7m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Host Nathan Latka interviews RIA in a Box CEO Will Bressman on acquiring a legacy compliance consulting agency through a Stanford search fund and scaling it into a SaaS business generating over $750,000 in monthly recurring revenue. Bressman shares insights on the firm's compliance software, unit economics, and 2018 private equity recapitalization with Aquiline Capital Partners.

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 42.8% of the talking time here. How this is scored →

Nathan as informed peer 5.0 Guest teaching 2.0 Guest disagreement 1.0 Nathan pushing back 3.4
05100:0010:001:12–3:52 · Nathan as informed peer 4/10 Core Product and RIA Compliance Value Proposition Latka asks standard discovery questions regarding RIA in a Box's core compliance software offering. Bressman clearly articulates the operational friction independent financial advisors face with SEC filings.3:52–8:53 · Nathan as informed peer 6/10 Pricing Structure and Monthly Recurring Revenue Latka demonstrates deep familiarity with Stanford search funds and agency valuation multiples. He presses Bressman when he notices him smiling about back-of-the-napkin MRR calculations.8:57–13:58 · Nathan as informed peer 6/10 Promotional Announcement: Growth Marketing Conference After an opening conference promo monologue, Latka interrogates the private equity buyout from Aqualine. Latka openly challenges Bressman's rationale for remaining CEO rather than raising a larger fund, prompting Bressman to defend his commitment.13:58–16:53 · Nathan as informed peer 7/10 Retention Metrics, Customer Acquisition Cost, and Content Marketing Latka instantly catches a mathematical contradiction when Bressman claims gross retention is over 100 percent. Latka forces a quick correction to net retention and calculates required expansion rates on the fly.16:53–17:56 · Nathan as informed peer 2/10 The Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire closing segment with quick questions on books, CEOs, and tools.1:12–3:52 · Guest teaching 3/10 Core Product and RIA Compliance Value Proposition Latka asks standard discovery questions regarding RIA in a Box's core compliance software offering. Bressman clearly articulates the operational friction independent financial advisors face with SEC filings.3:52–8:53 · Guest teaching 2/10 Pricing Structure and Monthly Recurring Revenue Latka demonstrates deep familiarity with Stanford search funds and agency valuation multiples. He presses Bressman when he notices him smiling about back-of-the-napkin MRR calculations.8:57–13:58 · Guest teaching 2/10 Promotional Announcement: Growth Marketing Conference After an opening conference promo monologue, Latka interrogates the private equity buyout from Aqualine. Latka openly challenges Bressman's rationale for remaining CEO rather than raising a larger fund, prompting Bressman to defend his commitment.13:58–16:53 · Guest teaching 2/10 Retention Metrics, Customer Acquisition Cost, and Content Marketing Latka instantly catches a mathematical contradiction when Bressman claims gross retention is over 100 percent. Latka forces a quick correction to net retention and calculates required expansion rates on the fly.16:53–17:56 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire closing segment with quick questions on books, CEOs, and tools.1:12–3:52 · Guest disagreement 0/10 Core Product and RIA Compliance Value Proposition Latka asks standard discovery questions regarding RIA in a Box's core compliance software offering. Bressman clearly articulates the operational friction independent financial advisors face with SEC filings.3:52–8:53 · Guest disagreement 1/10 Pricing Structure and Monthly Recurring Revenue Latka demonstrates deep familiarity with Stanford search funds and agency valuation multiples. He presses Bressman when he notices him smiling about back-of-the-napkin MRR calculations.8:57–13:58 · Guest disagreement 3/10 Promotional Announcement: Growth Marketing Conference After an opening conference promo monologue, Latka interrogates the private equity buyout from Aqualine. Latka openly challenges Bressman's rationale for remaining CEO rather than raising a larger fund, prompting Bressman to defend his commitment.13:58–16:53 · Guest disagreement 1/10 Retention Metrics, Customer Acquisition Cost, and Content Marketing Latka instantly catches a mathematical contradiction when Bressman claims gross retention is over 100 percent. Latka forces a quick correction to net retention and calculates required expansion rates on the fly.16:53–17:56 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire closing segment with quick questions on books, CEOs, and tools.1:12–3:52 · Nathan pushing back 1/10 Core Product and RIA Compliance Value Proposition Latka asks standard discovery questions regarding RIA in a Box's core compliance software offering. Bressman clearly articulates the operational friction independent financial advisors face with SEC filings.3:52–8:53 · Nathan pushing back 4/10 Pricing Structure and Monthly Recurring Revenue Latka demonstrates deep familiarity with Stanford search funds and agency valuation multiples. He presses Bressman when he notices him smiling about back-of-the-napkin MRR calculations.8:57–13:58 · Nathan pushing back 6/10 Promotional Announcement: Growth Marketing Conference After an opening conference promo monologue, Latka interrogates the private equity buyout from Aqualine. Latka openly challenges Bressman's rationale for remaining CEO rather than raising a larger fund, prompting Bressman to defend his commitment.13:58–16:53 · Nathan pushing back 5/10 Retention Metrics, Customer Acquisition Cost, and Content Marketing Latka instantly catches a mathematical contradiction when Bressman claims gross retention is over 100 percent. Latka forces a quick correction to net retention and calculates required expansion rates on the fly.16:53–17:56 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire closing segment with quick questions on books, CEOs, and tools.

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

0:00 · Nathan 50.2% · guest 49.8%0:00 · Nathan 50.2% · guest 49.8%3:00 · Nathan 36% · guest 64%3:00 · Nathan 36% · guest 64%6:00 · Nathan 20% · guest 80%6:00 · Nathan 20% · guest 80%9:00 · Nathan 69.8% · guest 30.2%9:00 · Nathan 69.8% · guest 30.2%12:00 · Nathan 36.8% · guest 63.2%12:00 · Nathan 36.8% · guest 63.2%15:00 · Nathan 27.8% · guest 72.2%15:00 · Nathan 27.8% · guest 72.2%18:00 · Nathan 97.2% · guest 2.8%18:00 · Nathan 97.2% · guest 2.8%
Sharpest disagreement ▶ 12:25 Bressman defends staying at the company post-buyout

Bressman firmly rejects Latka's cynical assertion that he should have cashed out and raised a private fund, insisting on the tangible market opportunity ahead.

 Hardest push from Nathan ▶ 12:17 Latka calls disbelief on Bressman's motivations

Latka directly interrupts Bressman with 'Come on, Will. I don't believe you', refusing to accept his standard corporate line about staying on after the private equity buyout.

 Biggest teaching moment ▶ 2:41 Bressman explains SEC regulatory compliance barriers

Bressman educates Latka on why financial advisors spinning out from large institutions lack internal compliance officers and require automated statutory filing software.

 Nathan holds their own ▶ 14:26 Latka corrects retention metric logic

Latka immediately challenges Bressman's statement that gross revenue retention is over 100%, explaining that gross retention cannot exceed 100% and backing into the required expansion rate.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Core Product and RIA Compliance Value Proposition 4301 Latka asks standard discovery questions regarding RIA in a Box's core compliance software offering. Bressman clearly articulates the operational friction independent financial advisors face with SEC filings.
Pricing Structure and Monthly Recurring Revenue 6214 Latka demonstrates deep familiarity with Stanford search funds and agency valuation multiples. He presses Bressman when he notices him smiling about back-of-the-napkin MRR calculations.
Promotional Announcement: Growth Marketing Conference 6236 After an opening conference promo monologue, Latka interrogates the private equity buyout from Aqualine. Latka openly challenges Bressman's rationale for remaining CEO rather than raising a larger fund, prompting Bressman to defend his commitment.
Retention Metrics, Customer Acquisition Cost, and Content Marketing 7215 Latka instantly catches a mathematical contradiction when Bressman claims gross retention is over 100 percent. Latka forces a quick correction to net retention and calculates required expansion rates on the fly.
The Famous Five Rapid-Fire Questions 2101 A standard, friendly Famous Five rapid-fire closing segment with quick questions on books, CEOs, and tools.

Statements from this episode (13)

Assertion Supported
Bressman: Financial Advisors Are Increasingly Leaving Big Institutions to Go Independent
“You know, all that stuff is typically handled in house, but increasingly those advisors are going off and being independent.”
Will Bressman Dec 8, 2019 ▶ 2:08
Disclosure
Bressman: RIA in a Box pricing ranges from $5k to $15k annually
“So we're sort of in the range of like five to 15,000 per year.”
Will Bressman Dec 8, 2019 ▶ 3:53
Disclosure
Bressman: RIA in a Box makes directionally $750k monthly revenue
“It's directionally correct. Yeah.”
Will Bressman Dec 8, 2019 ▶ 4:28
Disclosure
RIA in a Box scaled via organic cash flow, not venture capital
“So it really follows more of the bootstrap path where we've grown through our own sort of internal reinvestment and money we've generated through the business as opposed to kind of tons and tons of VC rounds along the way.”
Will Bressman Dec 8, 2019 ▶ 5:10
Assertion Partly supported
Bressman acquired RIA in a Box in 2012 as pure consulting firm
“The company was started in 2000, in 2006, but we got involved in 2012. And you know, at that time he really had a consulting business that was not tech enabled. There was no real sort of internal or external technology”
Will Bressman Dec 8, 2019 ▶ 7:16
Disclosure
Bressman: RIA in a Box partnered with Aquiline Capital Partners
“We partnered with a private equity firm here in New York called Aqualine Capital Partners, and the idea really with joining with them was to give us that next phase of capital and really kind of expand our capabilities and our ability to serve the market.”
Will Bressman Dec 8, 2019 ▶ 10:47
Assertion Not checkable as stated
Bressman: RIA in a Box serves 1,800 of 30,000 potential firms
“We're working about 1800 firms. There's roughly 30,000 or so we can be working with.”
Will Bressman Dec 8, 2019 ▶ 12:29
Assertion Not checkable as stated
Bressman: RIA in a Box grows 30% to 50% year-over-year
“We're in that 30, 50% range.”
Will Bressman Dec 8, 2019 ▶ 13:14
Assertion Not checkable as stated
Bressman: RIA in a Box employs about 45 people
“We have about 45 people.”
Will Bressman Dec 8, 2019 ▶ 13:26
Assertion Not checkable as stated
Bressman: RIA in a Box Gross Retention Exceeds 90%
“We're above sort of 90% in gross retention and even higher in what we call preventable retention.”
Will Bressman Dec 8, 2019 ▶ 14:11
Assertion Not checkable as stated
Bressman: RIA in a Box Has CAC Payback of Under a Year
“We typically operate in sort of a year or less as our payback.”
Will Bressman Dec 8, 2019 ▶ 15:57
Assertion Not checkable as stated
Bressman: Content Marketing Is RIA in a Box's Primary Acquisition Driver
“But our primary customer acquisition channel has really been content. And for us that's just been a huge driver of growth in our business.”
Will Bressman Dec 8, 2019 ▶ 16:42
Assertion Not checkable as stated
Bressman: RIA in a Box Is Cash Flow Positive
“Yeah, we are.”
Will Bressman Dec 8, 2019 ▶ 16:51
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