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Feb 18, 2022 · 16m · top-founders

How He Patiently Bootstrapped To $4.5m in Revenue In Legacy Space

John Brakey · 9m spoken Nathan Latka · 4m spoken
0:00 / 0:00

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

In this interview, host Nathan Latka speaks with John Brakey, founder and CEO of Promys, exploring how he patiently bootstrapped an all-in-one PSA and CRM platform for IT integrators to over $4.1 million in ARR with an exceptionally lean 15-person team.

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 34.3% of the talking time here. How this is scored →

Nathan as informed peer 5.4 Guest teaching 2.6 Guest disagreement 1.4 Nathan pushing back 2.8
05100:0010:001:12–3:30 · Nathan as informed peer 5/10 Origins in IT Integration and Solving Operational Leakage Nathan presses John to give concrete company names rather than vague generalities. He then synthesizes John's explanation into a concise summary of the software's core value proposition for agencies.3:31–6:22 · Nathan as informed peer 6/10 Bootstrapped Financing and Corporate Ownership Structure Nathan drills down into the cap table and performs quick mental math on seat counts and blended pricing to determine average monthly contract value.6:23–9:01 · Nathan as informed peer 6/10 Customer Base, Headcount Structure, and Revenue Milestones John corrects Nathan when he mistakenly assumes the company only employs three people total. Nathan quickly recalibrates and calculates the monthly run rate of $345k.9:03–12:59 · Nathan as informed peer 7/10 Outbound Prospecting Strategy and Capital Efficiency Nathan demonstrates SaaS benchmarking knowledge by calculating revenue per head at $276k and placing them in the top quartile. He then pushes John to name potential strategic acquirers and market comparables.12:59–15:34 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions Nathan steers the rapid-fire questionnaire efficiently, intervening when John begins a lengthy discussion on behavioral psychology to keep the segment moving.1:12–3:30 · Guest teaching 3/10 Origins in IT Integration and Solving Operational Leakage Nathan presses John to give concrete company names rather than vague generalities. He then synthesizes John's explanation into a concise summary of the software's core value proposition for agencies.3:31–6:22 · Guest teaching 1/10 Bootstrapped Financing and Corporate Ownership Structure Nathan drills down into the cap table and performs quick mental math on seat counts and blended pricing to determine average monthly contract value.6:23–9:01 · Guest teaching 4/10 Customer Base, Headcount Structure, and Revenue Milestones John corrects Nathan when he mistakenly assumes the company only employs three people total. Nathan quickly recalibrates and calculates the monthly run rate of $345k.9:03–12:59 · Guest teaching 3/10 Outbound Prospecting Strategy and Capital Efficiency Nathan demonstrates SaaS benchmarking knowledge by calculating revenue per head at $276k and placing them in the top quartile. He then pushes John to name potential strategic acquirers and market comparables.12:59–15:34 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions Nathan steers the rapid-fire questionnaire efficiently, intervening when John begins a lengthy discussion on behavioral psychology to keep the segment moving.1:12–3:30 · Guest disagreement 1/10 Origins in IT Integration and Solving Operational Leakage Nathan presses John to give concrete company names rather than vague generalities. He then synthesizes John's explanation into a concise summary of the software's core value proposition for agencies.3:31–6:22 · Guest disagreement 1/10 Bootstrapped Financing and Corporate Ownership Structure Nathan drills down into the cap table and performs quick mental math on seat counts and blended pricing to determine average monthly contract value.6:23–9:01 · Guest disagreement 2/10 Customer Base, Headcount Structure, and Revenue Milestones John corrects Nathan when he mistakenly assumes the company only employs three people total. Nathan quickly recalibrates and calculates the monthly run rate of $345k.9:03–12:59 · Guest disagreement 2/10 Outbound Prospecting Strategy and Capital Efficiency Nathan demonstrates SaaS benchmarking knowledge by calculating revenue per head at $276k and placing them in the top quartile. He then pushes John to name potential strategic acquirers and market comparables.12:59–15:34 · Guest disagreement 1/10 The Famous Five Rapid-Fire Questions Nathan steers the rapid-fire questionnaire efficiently, intervening when John begins a lengthy discussion on behavioral psychology to keep the segment moving.1:12–3:30 · Nathan pushing back 3/10 Origins in IT Integration and Solving Operational Leakage Nathan presses John to give concrete company names rather than vague generalities. He then synthesizes John's explanation into a concise summary of the software's core value proposition for agencies.3:31–6:22 · Nathan pushing back 2/10 Bootstrapped Financing and Corporate Ownership Structure Nathan drills down into the cap table and performs quick mental math on seat counts and blended pricing to determine average monthly contract value.6:23–9:01 · Nathan pushing back 3/10 Customer Base, Headcount Structure, and Revenue Milestones John corrects Nathan when he mistakenly assumes the company only employs three people total. Nathan quickly recalibrates and calculates the monthly run rate of $345k.9:03–12:59 · Nathan pushing back 3/10 Outbound Prospecting Strategy and Capital Efficiency Nathan demonstrates SaaS benchmarking knowledge by calculating revenue per head at $276k and placing them in the top quartile. He then pushes John to name potential strategic acquirers and market comparables.12:59–15:34 · Nathan pushing back 3/10 The Famous Five Rapid-Fire Questions Nathan steers the rapid-fire questionnaire efficiently, intervening when John begins a lengthy discussion on behavioral psychology to keep the segment moving.

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

0:00 · Nathan 39.2% · guest 60.8%0:00 · Nathan 39.2% · guest 60.8%3:00 · Nathan 33.7% · guest 66.3%3:00 · Nathan 33.7% · guest 66.3%6:00 · Nathan 52% · guest 48%6:00 · Nathan 52% · guest 48%9:00 · Nathan 29.4% · guest 70.6%9:00 · Nathan 29.4% · guest 70.6%12:00 · Nathan 11.8% · guest 88.2%12:00 · Nathan 11.8% · guest 88.2%15:00 · Nathan 52.1% · guest 47.9%15:00 · Nathan 52.1% · guest 47.9%
Sharpest disagreement ▶ 7:09 Guest rejects team size assumption

John immediately steps in to clarify that three people refers only to sales reps, correcting Nathan's assumption about overall operational staffing.

 Hardest push from Nathan ▶ 1:38 Host demands concrete case study

Nathan interrupts John's generic explanation to push him to name an actual company so the audience hears a concrete business story.

 Biggest teaching moment ▶ 7:09 Guest explains full staffing breakdown

John educates Nathan on the internal structure of Promys, breaking down total headcount between support, training, and frequent product releases.

 Nathan holds their own ▶ 10:19 Host benchmarks capital efficiency

Nathan showcases industry command by computing the company's revenue per head at $276,000 and benchmarking it against the top 25th percentile of SaaS businesses.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Origins in IT Integration and Solving Operational Leakage 5313 Nathan presses John to give concrete company names rather than vague generalities. He then synthesizes John's explanation into a concise summary of the software's core value proposition for agencies.
Bootstrapped Financing and Corporate Ownership Structure 6112 Nathan drills down into the cap table and performs quick mental math on seat counts and blended pricing to determine average monthly contract value.
Customer Base, Headcount Structure, and Revenue Milestones 6423 John corrects Nathan when he mistakenly assumes the company only employs three people total. Nathan quickly recalibrates and calculates the monthly run rate of $345k.
Outbound Prospecting Strategy and Capital Efficiency 7323 Nathan demonstrates SaaS benchmarking knowledge by calculating revenue per head at $276k and placing them in the top quartile. He then pushes John to name potential strategic acquirers and market comparables.
The Famous Five Rapid-Fire Questions 3213 Nathan steers the rapid-fire questionnaire efficiently, intervening when John begins a lengthy discussion on behavioral psychology to keep the segment moving.

Statements from this episode (12)

Insight
Brakey: Most tech-integrator profit comes from services, not product sales
“And so if you think about a company that's doing service-based business, most of their profitability comes from their services, not from the product sales that they do.”
John Brakey Feb 18, 2022 ▶ 2:04
Assertion Not checkable as stated
Brakey: Most IT services firms use 2 to 4 fragmented software tools
“In addition to that, if you look at most people in the market, they're using two, three, sometimes four different products to cobble their business together, whether it's in the sales process, the order admin process, the delivery project services, and the tic…”
John Brakey Feb 18, 2022 ▶ 2:52
Disclosure
Brakey: Promys blended seat pricing averages roughly $59 per month
“It's based on a seat license and there are two seat licenses. There's a field license or technical license and a full license for the salespeople and the admin people. And so you're looking at it on average about if you blend those two rates together, about 59…”
John Brakey Feb 18, 2022 ▶ 4:45
Disclosure
Brakey: The average Promys customer has 40 to 45 seats
“The average customer is about 40, 45.”
John Brakey Feb 18, 2022 ▶ 5:09
Disclosure
Brakey: Promys operates with a three-person remote sales team
“No, there's only about three, and we do a lot of through marketing and referral. And like all of our sales are done remotely.”
John Brakey Feb 18, 2022 ▶ 5:25
Assertion Not checkable as stated
Brakey: Most Promys customers remain for 5+ years
“Most of our customers have been around for five plus years. In that case, some of the larger ones have been around for almost 10 years.”
John Brakey Feb 18, 2022 ▶ 6:39
Assertion Not checkable as stated
Brakey: Promys has approximately 150 to 200 customers
“So we both have I guess approximately about a 152 hundred.”
John Brakey Feb 18, 2022 ▶ 6:59
Assertion Not checkable as stated
Brakey: Promys has 15 full-time employees and 5 subcontractors
“Oh, the total team's 15 plus another five that are subcontract on the, like, so that if you, it breaks down into support like customer service and so forth, implementation training, and the other part of it is the dev development.”
John Brakey Feb 18, 2022 ▶ 7:15
Assertion Not checkable as stated
Brakey: Promys generates about $345K in monthly revenue
“Yeah, that's about right.”
John Brakey Feb 18, 2022 ▶ 7:59
Assertion Not checkable as stated
Brakey: Promys revenue was roughly 25% lower one year ago
“We were probably about 25% less.”
John Brakey Feb 18, 2022 ▶ 8:06
Disclosure
Brakey: Promys funded growth through cash flow and prior business exits
“We've had a lot of good cashflow and we had our own investment from some other businesses that we sold. So we've never really had to go outside in the marketplace.”
John Brakey Feb 18, 2022 ▶ 10:08
Assertion Not checkable as stated
Brakey: ConnectWise struggled for 18 months after private equity acquisition
“Well, it was connect wise had a major problem when they had a major investor committed by the company and it took them about maybe a year and a half to really recover from that.”
John Brakey Feb 18, 2022 ▶ 11:49
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