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Dec 26, 2020 · 19m · top-founders

BossInsights 2x YoY to 5 Customers Helping Lenders Capture Data

Keren Moynihan · 10m spoken Nathan Latka · 6m 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 with Nathan Latka, Boss Insights CEO Keren Moynihan shares how her company provides an 800+ integration data bridge for commercial lenders while scaling toward $2M ARR through capital-efficient bootstrapping.

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 36.6% of the talking time here. How this is scored →

Nathan as informed peer 4.5 Guest teaching 2.5 Guest disagreement 2.3 Nathan pushing back 4.0
05100:0010:001:37–4:29 · Nathan as informed peer 5/10 Introducing Keren Moynihan and Boss Insights Nathan links the business model to known players like Cabbage and FounderPath. Keren playfully teases Nathan by referencing his own lending model.4:29–6:48 · Nathan as informed peer 4/10 Transforming Manual Due Diligence into Real-Time Decisions Nathan presses for average revenue per customer. Keren deflects citing enterprise confidentiality and pivots to efficiency metrics.6:48–8:55 · Nathan as informed peer 5/10 Funding Boss Insights with Non-Dilutive Capital Nathan probes how the company bootstrapped, clarifying whether they did a token sale versus mining crypto directly, and estimates non-dilutive grant sizes.8:55–14:04 · Nathan as informed peer 6/10 Equity Split, Technical Savants, and Team Growth Nathan pulls apart Keren's customer numbers by differentiating end borrowers from paying lenders, and reverse engineers her 2019-2020 revenue.14:04–16:52 · Nathan as informed peer 5/10 Industry Outlook: Collaboration and Infrastructure Over Silos Nathan challenges the build-versus-buy premise and questions if Boss Insights' 800 integrations are pre-built. Keren explains the necessity of data normalization across financial categories.16:52–19:08 · Nathan as informed peer 2/10 Famous Five Questions with Keren Moynihan In the Famous Five wrap-up, Keren playfully refuses to state her age, leading Nathan to rephrase his final advice question.1:37–4:29 · Guest teaching 3/10 Introducing Keren Moynihan and Boss Insights Nathan links the business model to known players like Cabbage and FounderPath. Keren playfully teases Nathan by referencing his own lending model.4:29–6:48 · Guest teaching 3/10 Transforming Manual Due Diligence into Real-Time Decisions Nathan presses for average revenue per customer. Keren deflects citing enterprise confidentiality and pivots to efficiency metrics.6:48–8:55 · Guest teaching 2/10 Funding Boss Insights with Non-Dilutive Capital Nathan probes how the company bootstrapped, clarifying whether they did a token sale versus mining crypto directly, and estimates non-dilutive grant sizes.8:55–14:04 · Guest teaching 2/10 Equity Split, Technical Savants, and Team Growth Nathan pulls apart Keren's customer numbers by differentiating end borrowers from paying lenders, and reverse engineers her 2019-2020 revenue.14:04–16:52 · Guest teaching 4/10 Industry Outlook: Collaboration and Infrastructure Over Silos Nathan challenges the build-versus-buy premise and questions if Boss Insights' 800 integrations are pre-built. Keren explains the necessity of data normalization across financial categories.16:52–19:08 · Guest teaching 1/10 Famous Five Questions with Keren Moynihan In the Famous Five wrap-up, Keren playfully refuses to state her age, leading Nathan to rephrase his final advice question.1:37–4:29 · Guest disagreement 2/10 Introducing Keren Moynihan and Boss Insights Nathan links the business model to known players like Cabbage and FounderPath. Keren playfully teases Nathan by referencing his own lending model.4:29–6:48 · Guest disagreement 3/10 Transforming Manual Due Diligence into Real-Time Decisions Nathan presses for average revenue per customer. Keren deflects citing enterprise confidentiality and pivots to efficiency metrics.6:48–8:55 · Guest disagreement 2/10 Funding Boss Insights with Non-Dilutive Capital Nathan probes how the company bootstrapped, clarifying whether they did a token sale versus mining crypto directly, and estimates non-dilutive grant sizes.8:55–14:04 · Guest disagreement 2/10 Equity Split, Technical Savants, and Team Growth Nathan pulls apart Keren's customer numbers by differentiating end borrowers from paying lenders, and reverse engineers her 2019-2020 revenue.14:04–16:52 · Guest disagreement 2/10 Industry Outlook: Collaboration and Infrastructure Over Silos Nathan challenges the build-versus-buy premise and questions if Boss Insights' 800 integrations are pre-built. Keren explains the necessity of data normalization across financial categories.16:52–19:08 · Guest disagreement 3/10 Famous Five Questions with Keren Moynihan In the Famous Five wrap-up, Keren playfully refuses to state her age, leading Nathan to rephrase his final advice question.1:37–4:29 · Nathan pushing back 2/10 Introducing Keren Moynihan and Boss Insights Nathan links the business model to known players like Cabbage and FounderPath. Keren playfully teases Nathan by referencing his own lending model.4:29–6:48 · Nathan pushing back 5/10 Transforming Manual Due Diligence into Real-Time Decisions Nathan presses for average revenue per customer. Keren deflects citing enterprise confidentiality and pivots to efficiency metrics.6:48–8:55 · Nathan pushing back 4/10 Funding Boss Insights with Non-Dilutive Capital Nathan probes how the company bootstrapped, clarifying whether they did a token sale versus mining crypto directly, and estimates non-dilutive grant sizes.8:55–14:04 · Nathan pushing back 6/10 Equity Split, Technical Savants, and Team Growth Nathan pulls apart Keren's customer numbers by differentiating end borrowers from paying lenders, and reverse engineers her 2019-2020 revenue.14:04–16:52 · Nathan pushing back 4/10 Industry Outlook: Collaboration and Infrastructure Over Silos Nathan challenges the build-versus-buy premise and questions if Boss Insights' 800 integrations are pre-built. Keren explains the necessity of data normalization across financial categories.16:52–19:08 · Nathan pushing back 3/10 Famous Five Questions with Keren Moynihan In the Famous Five wrap-up, Keren playfully refuses to state her age, leading Nathan to rephrase his final advice question.

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

0:00 · Nathan 68.8% · guest 31.2%0:00 · Nathan 68.8% · guest 31.2%3:00 · Nathan 22.3% · guest 77.7%3:00 · Nathan 22.3% · guest 77.7%6:00 · Nathan 32.1% · guest 67.9%6:00 · Nathan 32.1% · guest 67.9%9:00 · Nathan 39.1% · guest 60.9%9:00 · Nathan 39.1% · guest 60.9%12:00 · Nathan 30.2% · guest 69.8%12:00 · Nathan 30.2% · guest 69.8%15:00 · Nathan 22.1% · guest 77.9%15:00 · Nathan 22.1% · guest 77.9%18:00 · Nathan 48.8% · guest 51.2%18:00 · Nathan 48.8% · guest 51.2%
Sharpest disagreement ▶ 17:55 Keren refuses age question

Keren bluntly pushes back against Nathan's personal question, joking that asking her age is rude.

 Hardest push from Nathan ▶ 11:22 Nathan presses on real paying customer count

Nathan refuses Keren's framing of having thousands of customers by clarifying that borrowers do not pay her, isolating the true number of paying lenders.

 Biggest teaching moment ▶ 15:30 Keren educates on API normalization limits

Keren breaks down why building in-house works for one to three connections but fails when normalizing data across multi-category commerce and banking.

 Nathan holds their own ▶ 13:31 Nathan reverse engineers historical revenue

Nathan deduces Keren's approximate 2019 and 2020 revenue based on her growth rates and run rate targets, prompting Keren to call his precision surgical.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Keren Moynihan and Boss Insights 5322 Nathan links the business model to known players like Cabbage and FounderPath. Keren playfully teases Nathan by referencing his own lending model.
Transforming Manual Due Diligence into Real-Time Decisions 4335 Nathan presses for average revenue per customer. Keren deflects citing enterprise confidentiality and pivots to efficiency metrics.
Funding Boss Insights with Non-Dilutive Capital 5224 Nathan probes how the company bootstrapped, clarifying whether they did a token sale versus mining crypto directly, and estimates non-dilutive grant sizes.
Equity Split, Technical Savants, and Team Growth 6226 Nathan pulls apart Keren's customer numbers by differentiating end borrowers from paying lenders, and reverse engineers her 2019-2020 revenue.
Industry Outlook: Collaboration and Infrastructure Over Silos 5424 Nathan challenges the build-versus-buy premise and questions if Boss Insights' 800 integrations are pre-built. Keren explains the necessity of data normalization across financial categories.
Famous Five Questions with Keren Moynihan 2133 In the Famous Five wrap-up, Keren playfully refuses to state her age, leading Nathan to rephrase his final advice question.

Statements from this episode (13)

Disclosure
Boss Insights charges lenders per borrower instead of by data query
“It's pure SaaS, and we're actually not charging by data because then we're a cost center. We're actually charging when we make the lenders win, so we charge per borrower. They make money, we make money.”
Keren Moynihan Dec 26, 2020 ▶ 2:09
Insight
Traditional lenders demand historical accounting while alternative lenders evaluate cash flow
“There are two main categories that lenders want right now. They're either traditional lenders, and what they want is accounting information, because the second a business says, I want money, they say, give me two years of financials, or they're an alternative …”
Keren Moynihan Dec 26, 2020 ▶ 3:51
Disclosure
Boss Insights volume-tiered pricing scales down to $1 per borrower
“We have economies of scale pricing. If you, we have ways for people to test this out. If they have one to 10 borrowers, let's say, but the sweet spot really happens when you get to a couple hundred and then it is under 20 dollars. We have pricing that goes dow…”
Keren Moynihan Dec 26, 2020 ▶ 5:36
Assertion Not checkable as stated
Boss Insights helped CC Bank cut loan processing time by 80%
“A recent quote we got from CC Bank, for example, is that in 30 to 60 days, they got access to two to three years worth of leads. They decreased the amount of time they were spending by 80%.”
Keren Moynihan Dec 26, 2020 ▶ 6:33
Disclosure
Boss Insights funded a non-dilutive $1M seed round by mining Litecoin
“The first money in Boston insights was mined in a basement. And still yet, we haven't diluted. We have, we've essentially raised a seed round, almost a million dollars, but we haven't diluted at all.”
Keren Moynihan Dec 26, 2020 ▶ 7:17
Disclosure
Boss Insights has zero outside investors on its cap table
“The cap table is really healthy. There's no investors on it.”
Keren Moynihan Dec 26, 2020 ▶ 9:09
Disclosure
Boss Insights co-founders split equity 51% to 49%
“51 49.”
Keren Moynihan Dec 26, 2020 ▶ 9:35
Disclosure
Boss Insights seeks a $1.5M strategic round from commercial lenders
“We have, we always say we would raise a million and a half. We already have the product built. But what we're looking for is not just capital. We want strategic. We want to work with lenders who really see that the market is changing and you need to be ahead o…”
Keren Moynihan Dec 26, 2020 ▶ 12:56
Assertion Not checkable as stated
Boss Insights doubled revenue in 2020 and projects tripling soon
“All the sales I'm talking about happened in 2019. And then we doubled it in 2020, and we're looking to triple that in the next few months.”
Keren Moynihan Dec 26, 2020 ▶ 13:24
Insight
Fintechs and traditional banks will fail unless they actively collaborate
“What we need to do as an industry is collaborate. We keep thinking of this as a competitive game and yes, it's a competitive game, but if we don't collaborate, we're all going to fail.”
Keren Moynihan Dec 26, 2020 ▶ 14:09
Insight
Normalizing data across more than three software integrations requires dedicated teams
“If you want one to three integrations, go build. And there, some of them are quite easy, like QuickBooks. But if you want to normalize data within a category, so if you want any more than three in accounting, you need to have an API shop to normalize the infor…”
Keren Moynihan Dec 26, 2020 ▶ 15:35
Assertion Not checkable as stated
Boss Insights has fully built all 800 integrations advertised online
“No, all those were actually built.”
Keren Moynihan Dec 26, 2020 ▶ 16:23
Prediction Not checkable as stated
Lenders will eventually evaluate business borrowers by merit rather than collateral
“There's going to be a point in time where we can measure business owners on their merit, not their collateral.”
Keren Moynihan Dec 26, 2020 ▶ 18:25
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