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Jul 27, 2019 · 22m · top-founders

1463 He's Wealthfront, Robinhood, Betterment Worst Nightmare helping Banks retain deposits

Rob Heiser · 12m spoken Nathan Latka · 7m spoken
0:00 / 0:00

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In this episode of The Top Entrepreneurs Podcast, host Nathan Latka interviews Segment CEO Rob Heiser on how his 24-person fintech company raised $30 million to turn raw transaction data into proactive intelligence that helps legacy banks retain deposits from digital wealth apps.

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 35.2% of the talking time here. How this is scored →

Nathan as informed peer 4.0 Guest teaching 2.9 Guest disagreement 1.4 Nathan pushing back 2.6
05100:0010:0020:000:00–2:06 · Nathan as informed peer 0/10 Promoting How to Be a Capitalist Without Any Capital Solo host introduction, book promotion, and episode teaser. Zero host-guest interaction.2:07–4:08 · Nathan as informed peer 4/10 Introduction to Rob Heiser and Segment's Platform Nathan invites Rob to describe Segment's platform and core revenue model. Rob explains transaction data ingestion, cleansing, and their per-account monthly billing structure.4:08–6:54 · Nathan as informed peer 7/10 Analyzing Pricing Models and Reseller Margins Nathan presses for specific ACV averages while Rob resists to protect reseller partner margins. Nathan pushes back forcefully on the broad ranges and challenges Rob's definition of annual PDF reports as true SaaS.6:54–10:10 · Nathan as informed peer 6/10 Company Inception and Raising Thirty Million in Venture Capital Rob outlines raising $30M in capital to fund upfront banking integrations. Nathan clarifies direct customer counts versus downstream reseller accounts and playfully ribs Rob about minimizing his team size.10:10–13:46 · Nathan as informed peer 5/10 Library Science Data Cleansing and the Robinhood Case Study Rob educates Nathan on the distinction between library science and conventional data science, illustrating with a concrete example of detecting sub-dollar verification transfers to Robinhood.13:46–17:10 · Nathan as informed peer 5/10 Growth Trajectory, Breakeven Milestones, and Partner Acquisition Costs Rob declines exact top-line revenue but shares metrics around doubling ARR, approaching breakeven, and 9-month sales cycles with legal-heavy payback periods.17:10–19:11 · Nathan as informed peer 6/10 Retention Mechanics, Customer Expansion, and Bank Mergers Nathan drills into churn mechanics, questioning Rob's assertion that customer churn only happens during bank M&A. Nathan pushes repeatedly to confirm whether any account ever downgrades spend.19:11–21:43 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions Standard Famous Five sequence covering book recommendations, local CEOs, work habits, and sleep schedules in a cooperative tone.21:43–22:13 · Nathan as informed peer 0/10 Episode Summary and Conclusion Host wraps up the episode with a recap monologue highlighting Segment's Robinhood deposit-saving value proposition.0:00–2:06 · Guest teaching 0/10 Promoting How to Be a Capitalist Without Any Capital Solo host introduction, book promotion, and episode teaser. Zero host-guest interaction.2:07–4:08 · Guest teaching 4/10 Introduction to Rob Heiser and Segment's Platform Nathan invites Rob to describe Segment's platform and core revenue model. Rob explains transaction data ingestion, cleansing, and their per-account monthly billing structure.4:08–6:54 · Guest teaching 3/10 Analyzing Pricing Models and Reseller Margins Nathan presses for specific ACV averages while Rob resists to protect reseller partner margins. Nathan pushes back forcefully on the broad ranges and challenges Rob's definition of annual PDF reports as true SaaS.6:54–10:10 · Guest teaching 4/10 Company Inception and Raising Thirty Million in Venture Capital Rob outlines raising $30M in capital to fund upfront banking integrations. Nathan clarifies direct customer counts versus downstream reseller accounts and playfully ribs Rob about minimizing his team size.10:10–13:46 · Guest teaching 7/10 Library Science Data Cleansing and the Robinhood Case Study Rob educates Nathan on the distinction between library science and conventional data science, illustrating with a concrete example of detecting sub-dollar verification transfers to Robinhood.13:46–17:10 · Guest teaching 3/10 Growth Trajectory, Breakeven Milestones, and Partner Acquisition Costs Rob declines exact top-line revenue but shares metrics around doubling ARR, approaching breakeven, and 9-month sales cycles with legal-heavy payback periods.17:10–19:11 · Guest teaching 3/10 Retention Mechanics, Customer Expansion, and Bank Mergers Nathan drills into churn mechanics, questioning Rob's assertion that customer churn only happens during bank M&A. Nathan pushes repeatedly to confirm whether any account ever downgrades spend.19:11–21:43 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions Standard Famous Five sequence covering book recommendations, local CEOs, work habits, and sleep schedules in a cooperative tone.21:43–22:13 · Guest teaching 0/10 Episode Summary and Conclusion Host wraps up the episode with a recap monologue highlighting Segment's Robinhood deposit-saving value proposition.0:00–2:06 · Guest disagreement 0/10 Promoting How to Be a Capitalist Without Any Capital Solo host introduction, book promotion, and episode teaser. Zero host-guest interaction.2:07–4:08 · Guest disagreement 0/10 Introduction to Rob Heiser and Segment's Platform Nathan invites Rob to describe Segment's platform and core revenue model. Rob explains transaction data ingestion, cleansing, and their per-account monthly billing structure.4:08–6:54 · Guest disagreement 5/10 Analyzing Pricing Models and Reseller Margins Nathan presses for specific ACV averages while Rob resists to protect reseller partner margins. Nathan pushes back forcefully on the broad ranges and challenges Rob's definition of annual PDF reports as true SaaS.6:54–10:10 · Guest disagreement 2/10 Company Inception and Raising Thirty Million in Venture Capital Rob outlines raising $30M in capital to fund upfront banking integrations. Nathan clarifies direct customer counts versus downstream reseller accounts and playfully ribs Rob about minimizing his team size.10:10–13:46 · Guest disagreement 1/10 Library Science Data Cleansing and the Robinhood Case Study Rob educates Nathan on the distinction between library science and conventional data science, illustrating with a concrete example of detecting sub-dollar verification transfers to Robinhood.13:46–17:10 · Guest disagreement 2/10 Growth Trajectory, Breakeven Milestones, and Partner Acquisition Costs Rob declines exact top-line revenue but shares metrics around doubling ARR, approaching breakeven, and 9-month sales cycles with legal-heavy payback periods.17:10–19:11 · Guest disagreement 3/10 Retention Mechanics, Customer Expansion, and Bank Mergers Nathan drills into churn mechanics, questioning Rob's assertion that customer churn only happens during bank M&A. Nathan pushes repeatedly to confirm whether any account ever downgrades spend.19:11–21:43 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Standard Famous Five sequence covering book recommendations, local CEOs, work habits, and sleep schedules in a cooperative tone.21:43–22:13 · Guest disagreement 0/10 Episode Summary and Conclusion Host wraps up the episode with a recap monologue highlighting Segment's Robinhood deposit-saving value proposition.0:00–2:06 · Nathan pushing back 0/10 Promoting How to Be a Capitalist Without Any Capital Solo host introduction, book promotion, and episode teaser. Zero host-guest interaction.2:07–4:08 · Nathan pushing back 1/10 Introduction to Rob Heiser and Segment's Platform Nathan invites Rob to describe Segment's platform and core revenue model. Rob explains transaction data ingestion, cleansing, and their per-account monthly billing structure.4:08–6:54 · Nathan pushing back 7/10 Analyzing Pricing Models and Reseller Margins Nathan presses for specific ACV averages while Rob resists to protect reseller partner margins. Nathan pushes back forcefully on the broad ranges and challenges Rob's definition of annual PDF reports as true SaaS.6:54–10:10 · Nathan pushing back 4/10 Company Inception and Raising Thirty Million in Venture Capital Rob outlines raising $30M in capital to fund upfront banking integrations. Nathan clarifies direct customer counts versus downstream reseller accounts and playfully ribs Rob about minimizing his team size.10:10–13:46 · Nathan pushing back 1/10 Library Science Data Cleansing and the Robinhood Case Study Rob educates Nathan on the distinction between library science and conventional data science, illustrating with a concrete example of detecting sub-dollar verification transfers to Robinhood.13:46–17:10 · Nathan pushing back 3/10 Growth Trajectory, Breakeven Milestones, and Partner Acquisition Costs Rob declines exact top-line revenue but shares metrics around doubling ARR, approaching breakeven, and 9-month sales cycles with legal-heavy payback periods.17:10–19:11 · Nathan pushing back 6/10 Retention Mechanics, Customer Expansion, and Bank Mergers Nathan drills into churn mechanics, questioning Rob's assertion that customer churn only happens during bank M&A. Nathan pushes repeatedly to confirm whether any account ever downgrades spend.19:11–21:43 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Standard Famous Five sequence covering book recommendations, local CEOs, work habits, and sleep schedules in a cooperative tone.21:43–22:13 · Nathan pushing back 0/10 Episode Summary and Conclusion Host wraps up the episode with a recap monologue highlighting Segment's Robinhood deposit-saving value proposition.

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

0:00 · Nathan 78.9% · guest 21.1%0:00 · Nathan 78.9% · guest 21.1%3:00 · Nathan 24.4% · guest 75.6%3:00 · Nathan 24.4% · guest 75.6%6:00 · Nathan 34.2% · guest 65.8%6:00 · Nathan 34.2% · guest 65.8%9:00 · Nathan 26.4% · guest 73.6%9:00 · Nathan 26.4% · guest 73.6%12:00 · Nathan 31.2% · guest 68.8%12:00 · Nathan 31.2% · guest 68.8%15:00 · Nathan 17.4% · guest 82.6%15:00 · Nathan 17.4% · guest 82.6%18:00 · Nathan 25.9% · guest 74.1%18:00 · Nathan 25.9% · guest 74.1%21:00 · Nathan 51.4% · guest 48.6%21:00 · Nathan 51.4% · guest 48.6%
Sharpest disagreement ▶ 5:13 Rob refuses to disclose reseller contract figures

Rob directly rejects Nathan's request for contract pricing, stating that answering would unfairly expose his channel partners' profit margins.

 Hardest push from Nathan ▶ 6:05 Nathan rejects classifying PDF deliverables as SaaS

Nathan bluntly refuses Rob's characterization of annual PDF reports as SaaS, reclassifying them as tech-enabled professional services and refocusing on pure software metrics.

 Biggest teaching moment ▶ 12:45 Rob explains micro-transaction detection to prevent churn

Rob walks through the exact mechanics of identifying sub-dollar account-linking micro-deposits from fintech disruptors like Robinhood before major capital outflows occur.

 Nathan holds their own ▶ 18:17 Nathan corners Rob on net revenue retention and downgrades

Nathan refuses to accept generic answers about bank mergers causing churn, methodically pressing until Rob explicitly states whether net revenue churn and plan downgrades ever occur.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Promoting How to Be a Capitalist Without Any Capital 0000 Solo host introduction, book promotion, and episode teaser. Zero host-guest interaction.
Introduction to Rob Heiser and Segment's Platform 4401 Nathan invites Rob to describe Segment's platform and core revenue model. Rob explains transaction data ingestion, cleansing, and their per-account monthly billing structure.
Analyzing Pricing Models and Reseller Margins 7357 Nathan presses for specific ACV averages while Rob resists to protect reseller partner margins. Nathan pushes back forcefully on the broad ranges and challenges Rob's definition of annual PDF reports as true SaaS.
Company Inception and Raising Thirty Million in Venture Capital 6424 Rob outlines raising $30M in capital to fund upfront banking integrations. Nathan clarifies direct customer counts versus downstream reseller accounts and playfully ribs Rob about minimizing his team size.
Library Science Data Cleansing and the Robinhood Case Study 5711 Rob educates Nathan on the distinction between library science and conventional data science, illustrating with a concrete example of detecting sub-dollar verification transfers to Robinhood.
Growth Trajectory, Breakeven Milestones, and Partner Acquisition Costs 5323 Rob declines exact top-line revenue but shares metrics around doubling ARR, approaching breakeven, and 9-month sales cycles with legal-heavy payback periods.
Retention Mechanics, Customer Expansion, and Bank Mergers 6336 Nathan drills into churn mechanics, questioning Rob's assertion that customer churn only happens during bank M&A. Nathan pushes repeatedly to confirm whether any account ever downgrades spend.
The Famous Five Rapid-Fire Questions 3201 Standard Famous Five sequence covering book recommendations, local CEOs, work habits, and sleep schedules in a cooperative tone.
Episode Summary and Conclusion 0000 Host wraps up the episode with a recap monologue highlighting Segment's Robinhood deposit-saving value proposition.

Statements from this episode (12)

Disclosure
Heiser: Most Segmint clients pay on a per-account-holder monthly basis
“The most traditional will with what most of our customers do is they pay us on a per customer per month basis. So basically account holder. And that's for our kind of end-to-end platform.”
Rob Heiser Jul 27, 2019 ▶ 3:17
Assertion Not checkable as stated
Heiser: Segmint serves banks from $200M assets up to top 50 institutions
“We have institutions as small as, you know, two or three hundred million in assets to institutions that are in the top 50 in the country.”
Rob Heiser Jul 27, 2019 ▶ 4:19
Assertion Not checkable as stated
Heiser: Segmint charges banks 5¢ to 20¢ per account per month
“So we charge anywhere from like a five to six cents based on what features are using in our product all the way up to 15, 20 cents per month. And that's on a per account basis. And it's also scales based on how many account quarters I have.”
Rob Heiser Jul 27, 2019 ▶ 6:31
Disclosure
Heiser: Segmint has raised over $30 million in outside capital
“Oh, we raised, we've raised over thirty million dollars.”
Rob Heiser Jul 27, 2019 ▶ 7:04
Disclosure
Heiser: Segmint serves a dozen direct institutions and 50+ via resellers
“So we have very small amount of direct customers, so we don't, again, we work with channels, so we probably have about a dozen or so institutions that we work with directly, but beyond that, we have, you know, over 50 institutions, if you're looking at that, i…”
Rob Heiser Jul 27, 2019 ▶ 8:31
Disclosure
Heiser: Segmint operates with a team of just 24 people
“We have 24 people.”
Rob Heiser Jul 27, 2019 ▶ 9:34
Assertion Not checkable as stated
Heiser: Segmint processes billions of financial transactions per year
“What we're doing on the library side is we're categorizing all that data, so we're seeing, you know, billions of transactions a year, and so we see those transactions and we're categorizing them both by the technology that we built, but”
Rob Heiser Jul 27, 2019 ▶ 10:47
Insight
Heiser: Once customer deposits move to fintech apps, they rarely return
“And from a bank perspective, once the money moves, it typically doesn't come back.”
Rob Heiser Jul 27, 2019 ▶ 13:20
Assertion Not checkable as stated
Heiser: Segmint is doubling ARR year over year
“And from an ARR, right? That's what everybody cares about. We're doubling about that every year. So we're looking at a double from an ARR perspective.”
Rob Heiser Jul 27, 2019 ▶ 14:27
Prediction Not checkable as stated
Heiser: Segmint will probably break even in early to mid-2019
“We're close. We'll, we'll probably break even sometime middle, middle to early next year.”
Rob Heiser Jul 27, 2019 ▶ 14:43
Assertion Not checkable as stated
Heiser: Segmint's enterprise partner sales cycle is about nine months
“Probably from a partner perspective to get all the way from a meeting to, you know, them signing up. It's probably about nine months.”
Rob Heiser Jul 27, 2019 ▶ 16:01
Assertion Not checkable as stated
Heiser: Segmint only loses banking clients via M&A
“You know, the funny thing is, is the only time that we've typically lost a client in our space is from acquisition. So obviously it's a lot of M&A is happening in banking and financial services. And that's typically, you know, you either win or lose on the M&A…”
Rob Heiser Jul 27, 2019 ▶ 17:21
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