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Feb 15, 2017 · 18m · top-founders

EP 571: SenaHill Transacted $200M In FinTech 2016, 7 Predictions for 2017 with Founding Partner Neil DeSena

Nathan Latka · 8m spoken Neil DeSena · 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

In Episode 571 of 'The Top,' host Nathan Latka interviews Neil DeSena, founding partner of SenaHill Partners, exploring how the merchant bank closed $200 million in 2016 transactions while examining 2017 FinTech trends across blockchain, bank infrastructure, and wealth management.

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 51.1% of the talking time here. How this is scored →

Nathan as informed peer 4.0 Guest teaching 3.6 Guest disagreement 1.2 Nathan pushing back 2.6
05100:0010:001:55–4:46 · Nathan as informed peer 4/10 SenaHill Investment Thesis and Wall Street's Knowledge Void Nathan prompts Neil on SenaHill's investment thesis and gently pushes him for an estimated 2016 transaction volume when Neil does not recall the exact figure. Neil educates the host on the post-2008 financial crisis brain drain on Wall Street.4:46–7:26 · Nathan as informed peer 4/10 2017 Outlook on Distributed Ledgers and Symbiont The conversation is collaborative as Nathan validates the utility thesis of distributed ledgers. Neil details portfolio company Symbiont's partnership with the state of Delaware to enable digital corporate registration.7:26–9:59 · Nathan as informed peer 3/10 Regulatory Shifts and Modernizing Bank Infrastructure Nathan asks for specific regulatory predictions under the incoming administration, which Neil candidly admits is outside his expertise. Neil then explains how banks are choking on legacy technology, spending 75% of IT budgets on maintenance.9:59–14:14 · Nathan as informed peer 7/10 Baby Boomer Wealth Transfer, Quant Trading, and InsurTech Nathan demonstrates significant subject-matter expertise by citing Wealthfront's AUM, daily tax-loss harvesting advantage, and comparison to Vanguard passive funds. Neil responds by noting that many startups over-index on cash-poor millennials while ignoring the massive baby boomer wealth transfer.14:14–17:21 · Nathan as informed peer 2/10 SenaHill Merchant Banking Model and The Famous Five During the Famous Five, Neil resists standard executive reading tropes and instead attributes his learning to his tenure at Spear Leeds & Kellogg and mentorship from Duncan Niederauer.1:55–4:46 · Guest teaching 4/10 SenaHill Investment Thesis and Wall Street's Knowledge Void Nathan prompts Neil on SenaHill's investment thesis and gently pushes him for an estimated 2016 transaction volume when Neil does not recall the exact figure. Neil educates the host on the post-2008 financial crisis brain drain on Wall Street.4:46–7:26 · Guest teaching 4/10 2017 Outlook on Distributed Ledgers and Symbiont The conversation is collaborative as Nathan validates the utility thesis of distributed ledgers. Neil details portfolio company Symbiont's partnership with the state of Delaware to enable digital corporate registration.7:26–9:59 · Guest teaching 4/10 Regulatory Shifts and Modernizing Bank Infrastructure Nathan asks for specific regulatory predictions under the incoming administration, which Neil candidly admits is outside his expertise. Neil then explains how banks are choking on legacy technology, spending 75% of IT budgets on maintenance.9:59–14:14 · Guest teaching 4/10 Baby Boomer Wealth Transfer, Quant Trading, and InsurTech Nathan demonstrates significant subject-matter expertise by citing Wealthfront's AUM, daily tax-loss harvesting advantage, and comparison to Vanguard passive funds. Neil responds by noting that many startups over-index on cash-poor millennials while ignoring the massive baby boomer wealth transfer.14:14–17:21 · Guest teaching 2/10 SenaHill Merchant Banking Model and The Famous Five During the Famous Five, Neil resists standard executive reading tropes and instead attributes his learning to his tenure at Spear Leeds & Kellogg and mentorship from Duncan Niederauer.1:55–4:46 · Guest disagreement 1/10 SenaHill Investment Thesis and Wall Street's Knowledge Void Nathan prompts Neil on SenaHill's investment thesis and gently pushes him for an estimated 2016 transaction volume when Neil does not recall the exact figure. Neil educates the host on the post-2008 financial crisis brain drain on Wall Street.4:46–7:26 · Guest disagreement 1/10 2017 Outlook on Distributed Ledgers and Symbiont The conversation is collaborative as Nathan validates the utility thesis of distributed ledgers. Neil details portfolio company Symbiont's partnership with the state of Delaware to enable digital corporate registration.7:26–9:59 · Guest disagreement 1/10 Regulatory Shifts and Modernizing Bank Infrastructure Nathan asks for specific regulatory predictions under the incoming administration, which Neil candidly admits is outside his expertise. Neil then explains how banks are choking on legacy technology, spending 75% of IT budgets on maintenance.9:59–14:14 · Guest disagreement 2/10 Baby Boomer Wealth Transfer, Quant Trading, and InsurTech Nathan demonstrates significant subject-matter expertise by citing Wealthfront's AUM, daily tax-loss harvesting advantage, and comparison to Vanguard passive funds. Neil responds by noting that many startups over-index on cash-poor millennials while ignoring the massive baby boomer wealth transfer.14:14–17:21 · Guest disagreement 1/10 SenaHill Merchant Banking Model and The Famous Five During the Famous Five, Neil resists standard executive reading tropes and instead attributes his learning to his tenure at Spear Leeds & Kellogg and mentorship from Duncan Niederauer.1:55–4:46 · Nathan pushing back 3/10 SenaHill Investment Thesis and Wall Street's Knowledge Void Nathan prompts Neil on SenaHill's investment thesis and gently pushes him for an estimated 2016 transaction volume when Neil does not recall the exact figure. Neil educates the host on the post-2008 financial crisis brain drain on Wall Street.4:46–7:26 · Nathan pushing back 1/10 2017 Outlook on Distributed Ledgers and Symbiont The conversation is collaborative as Nathan validates the utility thesis of distributed ledgers. Neil details portfolio company Symbiont's partnership with the state of Delaware to enable digital corporate registration.7:26–9:59 · Nathan pushing back 3/10 Regulatory Shifts and Modernizing Bank Infrastructure Nathan asks for specific regulatory predictions under the incoming administration, which Neil candidly admits is outside his expertise. Neil then explains how banks are choking on legacy technology, spending 75% of IT budgets on maintenance.9:59–14:14 · Nathan pushing back 4/10 Baby Boomer Wealth Transfer, Quant Trading, and InsurTech Nathan demonstrates significant subject-matter expertise by citing Wealthfront's AUM, daily tax-loss harvesting advantage, and comparison to Vanguard passive funds. Neil responds by noting that many startups over-index on cash-poor millennials while ignoring the massive baby boomer wealth transfer.14:14–17:21 · Nathan pushing back 2/10 SenaHill Merchant Banking Model and The Famous Five During the Famous Five, Neil resists standard executive reading tropes and instead attributes his learning to his tenure at Spear Leeds & Kellogg and mentorship from Duncan Niederauer.

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

0:00 · Nathan 76.4% · guest 23.6%0:00 · Nathan 76.4% · guest 23.6%3:00 · Nathan 40.3% · guest 59.7%3:00 · Nathan 40.3% · guest 59.7%6:00 · Nathan 32.1% · guest 67.9%6:00 · Nathan 32.1% · guest 67.9%9:00 · Nathan 40.3% · guest 59.7%9:00 · Nathan 40.3% · guest 59.7%12:00 · Nathan 39.1% · guest 60.9%12:00 · Nathan 39.1% · guest 60.9%15:00 · Nathan 72.3% · guest 27.7%15:00 · Nathan 72.3% · guest 27.7%18:00 · Nathan 100% · guest 0%18:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 12:14 Reframing fintech focus away from millennials

Neil pushes back against popular fintech industry assumptions, pointing out that millennials have no capital compared to the massive wealth transfer underway among retiring baby boomers.

 Hardest push from Nathan ▶ 4:25 Pressing for total 2016 transaction volume

When Neil does not recall SenaHill's 2016 deal volume offhand, Nathan refuses to let the metric slide and prompts him to establish a baseline floor number.

 Biggest teaching moment ▶ 2:49 Explaining the loss of institutional memory on Wall Street

Neil provides an in-depth breakdown of how the 2008 financial crisis eliminated generations of institutional trading knowledge, leaving a void for specialized advisory firms.

 Nathan holds their own ▶ 11:25 Nathan details robo-advisory tax loss harvesting metrics

Nathan demonstrates deep fintech knowledge by citing Wealthfront's $4.4B AUM and contrasting its automated daily tax-loss harvesting yields against traditional Vanguard index investing.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
SenaHill Investment Thesis and Wall Street's Knowledge Void 4413 Nathan prompts Neil on SenaHill's investment thesis and gently pushes him for an estimated 2016 transaction volume when Neil does not recall the exact figure. Neil educates the host on the post-2008 financial crisis brain drain on Wall Street.
2017 Outlook on Distributed Ledgers and Symbiont 4411 The conversation is collaborative as Nathan validates the utility thesis of distributed ledgers. Neil details portfolio company Symbiont's partnership with the state of Delaware to enable digital corporate registration.
Regulatory Shifts and Modernizing Bank Infrastructure 3413 Nathan asks for specific regulatory predictions under the incoming administration, which Neil candidly admits is outside his expertise. Neil then explains how banks are choking on legacy technology, spending 75% of IT budgets on maintenance.
Baby Boomer Wealth Transfer, Quant Trading, and InsurTech 7424 Nathan demonstrates significant subject-matter expertise by citing Wealthfront's AUM, daily tax-loss harvesting advantage, and comparison to Vanguard passive funds. Neil responds by noting that many startups over-index on cash-poor millennials while ignoring the massive baby boomer wealth transfer.
SenaHill Merchant Banking Model and The Famous Five 2212 During the Famous Five, Neil resists standard executive reading tropes and instead attributes his learning to his tenure at Spear Leeds & Kellogg and mentorship from Duncan Niederauer.

Statements from this episode (7)

Insight
DeSena: Post-2008 Wall Street lost generational knowledge of electronic transitions
“The knowledge that has seen the industry progress from a pure manual process to an electronic form, those guys are all gone. A lot of them are gone, and now you have much younger people filling that void, and there's a big bunch of stuff missing. Just a pure k…”
Neil DeSena Feb 15, 2017 ▶ 3:31
Assertion Not checkable as stated
DeSena: SenaHill advised or led close to $200M in 2016 transactions
“It was definitely more than a hundred million bucks. Close to two hundred million, I believe.”
Neil DeSena Feb 15, 2017 ▶ 4:32
Prediction Not checkable as stated
DeSena: Distributed ledger tech is ready for prime time in 2017
“It absolutely is ready for prime time. And I, it's ready for prime time for those who have built the technology proper. So I think this is going to be a year where the haves and the have nots are going to be distinguished.”
Neil DeSena Feb 15, 2017 ▶ 5:35
Assertion Contradicted
DeSena: Symbiont signed a deal with Delaware for digital company registration
“Well, they have signed a deal with the state of Delaware. And companies now are going to be able to register their companies digitally. So Symbiont is going to be at the point of formation of all of these companies.”
Neil DeSena Feb 15, 2017 ▶ 6:08
Prediction Not checkable as stated
DeSena predicts Wall Street regulations will ease under the Trump administration
“No, I think things are going to ease up, but that, that's not, that wasn't the rationale for me to put this here.”
Neil DeSena Feb 15, 2017 ▶ 7:39
Assertion Supported
DeSena: Banks spent $200B on tech in 2015, 75% on maintenance
“There was a report published that said in, I forgot who published it, but in. 15, two hundred billion dollars worldwide was spent by the banks in technology. 75% of that was basically maintenance.”
Neil DeSena Feb 15, 2017 ▶ 9:00
Opinion
DeSena: Portfolio company Tradelegs could replace Delta One desks at banks
“You could point to a company that we have called Tradelegs, which basically could replace the Delta one desks at all of the all of the big banks.”
Neil DeSena Feb 15, 2017 ▶ 9:45
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