Jul 31, 2017 · 25m · top-founders

737: 3000 Hotels Are Paying Them to Optimize Pricing, Investors Put in $50m

Patrick Bosworth · 15m spoken Nathan Latka · 8m spoken
0:00 / 0:00

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In this episode of The Top podcast, host Nathan Latka interviews Duetto Co-Founder and CEO Patrick Bosworth about scaling a hospitality revenue optimization SaaS platform to an approaching $50 million run rate across 3,000 hotels worldwide. Bosworth details Duetto's unit economics, co-founder recruitment, gross margin expansion from 30% to 75%, and the structural complexities of selling software into the lodging industry.

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 34.7% of the talking time here. How this is scored →

Nathan as informed peer 4.4 Guest teaching 3.8 Guest disagreement 2.1 Nathan pushing back 3.6
05100:0010:0020:001:21–4:12 · Nathan as informed peer 4/10 Educational Background and Leveraging Elite Networks Latka challenges the actual value of a Harvard MBA and asks whether the network can be hacked. Bosworth calmly breaks down the tangible benefits he received transitioning from the arts and politics, explaining exact costs and paths for executive alumni status.4:16–6:52 · Nathan as informed peer 5/10 Duetto's Core Platform and SaaS Monetization Model Latka probes Duetto's revenue model and questions why Bosworth found it surprising that hotels preferred fixed subscriptions over performance upside. Bosworth educates Latka on multi-stakeholder ownership structures in lodging that stall variable pricing negotiations.6:52–11:12 · Nathan as informed peer 6/10 Navigating Hospitality Stakeholders and Contract Sizing Latka presses aggressively on equity division among co-founders, calling equal splits weak and digging into CTO Craig Weissman's equity share. Bosworth answers openly, explaining how Weissman's involvement immediately multiplied their valuation fivefold.11:13–14:29 · Nathan as informed peer 6/10 Acquisition Economics, Sales Inefficiencies, and High Retention Latka calculates CAC from payback periods and asks why Duetto does not aggressively double CAC given near-zero churn. Bosworth schools Latka on lodging tech market dynamics, explaining that pouring sales cash in prematurely hits rigid multi-year incumbent contract cycles.14:30–18:31 · Nathan as informed peer 6/10 Global Expansion and Booking Recognition Mechanics Latka estimates a $50M run rate based on simple multiplication of hotel count by ACV. Bosworth corrects Latka by distinguishing gross contracted bookings from confirmed and deferred bookings due to custom integration timelines, also detailing COGS accounting for onboarding services.18:32–22:10 · Nathan as informed peer 6/10 Venture Capital Philosophy and Navigating Monthly Cash Burn Latka presses Bosworth on historic $1M monthly burn and VC expectations regarding idle balance sheet cash. Bosworth firmly rejects Latka's framing by distinguishing the 2015 growth-at-all-costs venture environment from the 2017 capital-efficiency regime.22:12–24:45 · Nathan as informed peer 2/10 Sponsor Break: Hotjar Website Analytics Platform Latka delivers an ad read for Hotjar and conducts the standard Famous Five rapid-fire questionnaire with concise, cooperative answers from Bosworth.24:46–25:44 · Nathan as informed peer 0/10 Episode Summary and Preview of Previous Guest Latka provides a solo recap of Duetto's key operating metrics and teases the upcoming episode.1:21–4:12 · Guest teaching 4/10 Educational Background and Leveraging Elite Networks Latka challenges the actual value of a Harvard MBA and asks whether the network can be hacked. Bosworth calmly breaks down the tangible benefits he received transitioning from the arts and politics, explaining exact costs and paths for executive alumni status.4:16–6:52 · Guest teaching 4/10 Duetto's Core Platform and SaaS Monetization Model Latka probes Duetto's revenue model and questions why Bosworth found it surprising that hotels preferred fixed subscriptions over performance upside. Bosworth educates Latka on multi-stakeholder ownership structures in lodging that stall variable pricing negotiations.6:52–11:12 · Guest teaching 3/10 Navigating Hospitality Stakeholders and Contract Sizing Latka presses aggressively on equity division among co-founders, calling equal splits weak and digging into CTO Craig Weissman's equity share. Bosworth answers openly, explaining how Weissman's involvement immediately multiplied their valuation fivefold.11:13–14:29 · Guest teaching 6/10 Acquisition Economics, Sales Inefficiencies, and High Retention Latka calculates CAC from payback periods and asks why Duetto does not aggressively double CAC given near-zero churn. Bosworth schools Latka on lodging tech market dynamics, explaining that pouring sales cash in prematurely hits rigid multi-year incumbent contract cycles.14:30–18:31 · Guest teaching 7/10 Global Expansion and Booking Recognition Mechanics Latka estimates a $50M run rate based on simple multiplication of hotel count by ACV. Bosworth corrects Latka by distinguishing gross contracted bookings from confirmed and deferred bookings due to custom integration timelines, also detailing COGS accounting for onboarding services.18:32–22:10 · Guest teaching 5/10 Venture Capital Philosophy and Navigating Monthly Cash Burn Latka presses Bosworth on historic $1M monthly burn and VC expectations regarding idle balance sheet cash. Bosworth firmly rejects Latka's framing by distinguishing the 2015 growth-at-all-costs venture environment from the 2017 capital-efficiency regime.22:12–24:45 · Guest teaching 1/10 Sponsor Break: Hotjar Website Analytics Platform Latka delivers an ad read for Hotjar and conducts the standard Famous Five rapid-fire questionnaire with concise, cooperative answers from Bosworth.24:46–25:44 · Guest teaching 0/10 Episode Summary and Preview of Previous Guest Latka provides a solo recap of Duetto's key operating metrics and teases the upcoming episode.1:21–4:12 · Guest disagreement 2/10 Educational Background and Leveraging Elite Networks Latka challenges the actual value of a Harvard MBA and asks whether the network can be hacked. Bosworth calmly breaks down the tangible benefits he received transitioning from the arts and politics, explaining exact costs and paths for executive alumni status.4:16–6:52 · Guest disagreement 2/10 Duetto's Core Platform and SaaS Monetization Model Latka probes Duetto's revenue model and questions why Bosworth found it surprising that hotels preferred fixed subscriptions over performance upside. Bosworth educates Latka on multi-stakeholder ownership structures in lodging that stall variable pricing negotiations.6:52–11:12 · Guest disagreement 2/10 Navigating Hospitality Stakeholders and Contract Sizing Latka presses aggressively on equity division among co-founders, calling equal splits weak and digging into CTO Craig Weissman's equity share. Bosworth answers openly, explaining how Weissman's involvement immediately multiplied their valuation fivefold.11:13–14:29 · Guest disagreement 3/10 Acquisition Economics, Sales Inefficiencies, and High Retention Latka calculates CAC from payback periods and asks why Duetto does not aggressively double CAC given near-zero churn. Bosworth schools Latka on lodging tech market dynamics, explaining that pouring sales cash in prematurely hits rigid multi-year incumbent contract cycles.14:30–18:31 · Guest disagreement 3/10 Global Expansion and Booking Recognition Mechanics Latka estimates a $50M run rate based on simple multiplication of hotel count by ACV. Bosworth corrects Latka by distinguishing gross contracted bookings from confirmed and deferred bookings due to custom integration timelines, also detailing COGS accounting for onboarding services.18:32–22:10 · Guest disagreement 4/10 Venture Capital Philosophy and Navigating Monthly Cash Burn Latka presses Bosworth on historic $1M monthly burn and VC expectations regarding idle balance sheet cash. Bosworth firmly rejects Latka's framing by distinguishing the 2015 growth-at-all-costs venture environment from the 2017 capital-efficiency regime.22:12–24:45 · Guest disagreement 1/10 Sponsor Break: Hotjar Website Analytics Platform Latka delivers an ad read for Hotjar and conducts the standard Famous Five rapid-fire questionnaire with concise, cooperative answers from Bosworth.24:46–25:44 · Guest disagreement 0/10 Episode Summary and Preview of Previous Guest Latka provides a solo recap of Duetto's key operating metrics and teases the upcoming episode.1:21–4:12 · Nathan pushing back 3/10 Educational Background and Leveraging Elite Networks Latka challenges the actual value of a Harvard MBA and asks whether the network can be hacked. Bosworth calmly breaks down the tangible benefits he received transitioning from the arts and politics, explaining exact costs and paths for executive alumni status.4:16–6:52 · Nathan pushing back 4/10 Duetto's Core Platform and SaaS Monetization Model Latka probes Duetto's revenue model and questions why Bosworth found it surprising that hotels preferred fixed subscriptions over performance upside. Bosworth educates Latka on multi-stakeholder ownership structures in lodging that stall variable pricing negotiations.6:52–11:12 · Nathan pushing back 6/10 Navigating Hospitality Stakeholders and Contract Sizing Latka presses aggressively on equity division among co-founders, calling equal splits weak and digging into CTO Craig Weissman's equity share. Bosworth answers openly, explaining how Weissman's involvement immediately multiplied their valuation fivefold.11:13–14:29 · Nathan pushing back 4/10 Acquisition Economics, Sales Inefficiencies, and High Retention Latka calculates CAC from payback periods and asks why Duetto does not aggressively double CAC given near-zero churn. Bosworth schools Latka on lodging tech market dynamics, explaining that pouring sales cash in prematurely hits rigid multi-year incumbent contract cycles.14:30–18:31 · Nathan pushing back 5/10 Global Expansion and Booking Recognition Mechanics Latka estimates a $50M run rate based on simple multiplication of hotel count by ACV. Bosworth corrects Latka by distinguishing gross contracted bookings from confirmed and deferred bookings due to custom integration timelines, also detailing COGS accounting for onboarding services.18:32–22:10 · Nathan pushing back 5/10 Venture Capital Philosophy and Navigating Monthly Cash Burn Latka presses Bosworth on historic $1M monthly burn and VC expectations regarding idle balance sheet cash. Bosworth firmly rejects Latka's framing by distinguishing the 2015 growth-at-all-costs venture environment from the 2017 capital-efficiency regime.22:12–24:45 · Nathan pushing back 2/10 Sponsor Break: Hotjar Website Analytics Platform Latka delivers an ad read for Hotjar and conducts the standard Famous Five rapid-fire questionnaire with concise, cooperative answers from Bosworth.24:46–25:44 · Nathan pushing back 0/10 Episode Summary and Preview of Previous Guest Latka provides a solo recap of Duetto's key operating metrics and teases the upcoming episode.

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

0:00 · Nathan 66.4% · guest 33.6%0:00 · Nathan 66.4% · guest 33.6%3:00 · Nathan 15.5% · guest 84.5%3:00 · Nathan 15.5% · guest 84.5%6:00 · Nathan 27.1% · guest 72.9%6:00 · Nathan 27.1% · guest 72.9%9:00 · Nathan 36.6% · guest 63.4%9:00 · Nathan 36.6% · guest 63.4%12:00 · Nathan 20.8% · guest 79.2%12:00 · Nathan 20.8% · guest 79.2%15:00 · Nathan 11.5% · guest 88.5%15:00 · Nathan 11.5% · guest 88.5%18:00 · Nathan 20.9% · guest 79.1%18:00 · Nathan 20.9% · guest 79.1%21:00 · Nathan 60.9% · guest 39.1%21:00 · Nathan 60.9% · guest 39.1%24:00 · Nathan 71.4% · guest 28.6%24:00 · Nathan 71.4% · guest 28.6%
Sharpest disagreement ▶ 21:48 Bosworth rejects Latka's board sentiment assumption

Bosworth sharply counters Latka's assertion that VCs would demand money back if it sat idle on the balance sheet, contrasting 2015 growth mandates with 2017 capital conservation.

Hardest push from Nathan ▶ 9:01 Latka challenges equal co-founder equity splits

Latka aggressively pushes back on standard polite equity splits, arguing that equal splits are weak and pressing Bosworth on who was valued higher.

Biggest teaching moment ▶ 14:46 Bosworth breaks down deferred vs confirmed bookings

Bosworth corrects Latka's top-line $50M run rate math, educating him on how integration lags in enterprise hospitality create significant delays between gross bookings and recognized revenue.

Nathan holds their own ▶ 11:30 Latka calculates CAC from ACV and payback period

Latka immediately calculates Duetto's estimated acquisition cost of $20,000 using Bosworth's stated 14-month payback period and $17,000 ACV.

the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Educational Background and Leveraging Elite Networks 4423 Latka challenges the actual value of a Harvard MBA and asks whether the network can be hacked. Bosworth calmly breaks down the tangible benefits he received transitioning from the arts and politics, explaining exact costs and paths for executive alumni status.
Duetto's Core Platform and SaaS Monetization Model 5424 Latka probes Duetto's revenue model and questions why Bosworth found it surprising that hotels preferred fixed subscriptions over performance upside. Bosworth educates Latka on multi-stakeholder ownership structures in lodging that stall variable pricing negotiations.
Navigating Hospitality Stakeholders and Contract Sizing 6326 Latka presses aggressively on equity division among co-founders, calling equal splits weak and digging into CTO Craig Weissman's equity share. Bosworth answers openly, explaining how Weissman's involvement immediately multiplied their valuation fivefold.
Acquisition Economics, Sales Inefficiencies, and High Retention 6634 Latka calculates CAC from payback periods and asks why Duetto does not aggressively double CAC given near-zero churn. Bosworth schools Latka on lodging tech market dynamics, explaining that pouring sales cash in prematurely hits rigid multi-year incumbent contract cycles.
Global Expansion and Booking Recognition Mechanics 6735 Latka estimates a $50M run rate based on simple multiplication of hotel count by ACV. Bosworth corrects Latka by distinguishing gross contracted bookings from confirmed and deferred bookings due to custom integration timelines, also detailing COGS accounting for onboarding services.
Venture Capital Philosophy and Navigating Monthly Cash Burn 6545 Latka presses Bosworth on historic $1M monthly burn and VC expectations regarding idle balance sheet cash. Bosworth firmly rejects Latka's framing by distinguishing the 2015 growth-at-all-costs venture environment from the 2017 capital-efficiency regime.
Sponsor Break: Hotjar Website Analytics Platform 2112 Latka delivers an ad read for Hotjar and conducts the standard Famous Five rapid-fire questionnaire with concise, cooperative answers from Bosworth.
Episode Summary and Preview of Previous Guest 0000 Latka provides a solo recap of Duetto's key operating metrics and teases the upcoming episode.

Statements from this episode (17)

What-if
Bosworth: Duetto Would Not Exist Without Harvard MBA
“I don't think the company would exist without it.”
Patrick Bosworth Jul 31, 2017 ▶ 1:50
Assertion Not checkable as stated
Bosworth: Duetto Boosts Hotel Revenue 6.5–8.5% and Profit 75–100%
“And in general, that increases their revenue by anywhere from six and a half to eight and a half percent, which increases their profit by 75 to a hundred percent.”
Patrick Bosworth Jul 31, 2017 ▶ 4:57
Insight
Bosworth: Variable Hotel SaaS Contracts Delay Negotiations by Months
“And so anytime we tried to do a more variable contract, a pricing negotiation that might take one to two weeks would drag on for one to two or three months.”
Patrick Bosworth Jul 31, 2017 ▶ 6:10
Disclosure
Bosworth: Variable Upside Accounts for At Most 7–8% of Duetto Revenue
“It may have been seven or eight percent, but no more than that.”
Patrick Bosworth Jul 31, 2017 ▶ 6:50
Insight
Bosworth: Hotel brands often neither own properties nor employ staff
“What a lot of people don't realize about the hotel industry today, though, Is that a lot of times the brand is no longer the operator. They've gone so asset light that they no longer, not only do they not own the underlying real estate, they also don't actuall…”
Patrick Bosworth Jul 31, 2017 ▶ 7:57
Assertion Not checkable as stated
Bosworth: Duetto makes $17k-$18k per hotel property annually
“So on a per property basis, I think today we're getting about 17 or 18,000 dollars per hotel per year.”
Patrick Bosworth Jul 31, 2017 ▶ 8:31
Assertion Not checkable as stated
Duetto's Valuation Jumped to $10M When Former Salesforce CTO Joined
“Marco and I were in Vegas at the time, and we were trying to raise money there. We were getting valuations more in the, you know, one to two million range. And the day that Craig joined, the valuations jumped up to the ten million dollar range.”
Patrick Bosworth Jul 31, 2017 ▶ 9:48
Disclosure
Bosworth: Craig Weissman is Duetto's largest common shareholder
“He is the largest common shareholder. He has a plurality, but not a majority.”
Patrick Bosworth Jul 31, 2017 ▶ 11:07
Assertion Not checkable as stated
Duetto has an estimated 14-month CAC payback period
“Our payback period is about 14 months right now.”
Patrick Bosworth Jul 31, 2017 ▶ 11:30
Assertion Not checkable as stated
Bosworth: Duetto has never lost a customer in five years
“We, we've literally never lost a company, a customer in five years.”
Patrick Bosworth Jul 31, 2017 ▶ 11:50
Insight
Bosworth: Hospitality SaaS cannot easily accelerate growth via additional sales spend
“There's almost this force of nature where it's actually really hard to grow the business faster than it's naturally growing because there are these time periods where a hotel company is looking for new technology either because they've bought one of our incumb…”
Patrick Bosworth Jul 31, 2017 ▶ 13:38
Prediction Not checkable as stated
Bosworth: Duetto will reach a $50 million run rate next year
“I don't usually share the exact numbers, but we're a fraction of the number that you just claimed, you know, the back of the envelope that you did, but we will be there next year.”
Patrick Bosworth Jul 31, 2017 ▶ 15:28
Assertion Not checkable as stated
Bosworth: Duetto gross margins rose to mid-70s from 30s in one year
“Now ours is hovering in the mid seventies. It's healthy, but a year ago was in the thirties.”
Patrick Bosworth Jul 31, 2017 ▶ 16:25
Assertion Not checkable as stated
Bosworth: Duetto platform gross margin exceeds 95% excluding services
“So our platform gross margin is north of 95%. Our blended gross margin, including, you know, the onboarding services is where it dips down into the seventies.”
Patrick Bosworth Jul 31, 2017 ▶ 17:46
Assertion Not checkable as stated
Bosworth: Duetto cash burn fell over 50% in 18 months
“Over the last 18 months has been more than cut in half, and we expect it to get cut in half again.”
Patrick Bosworth Jul 31, 2017 ▶ 18:27
Assertion Not checkable as stated
Duetto burned over $1M per month for a couple of years
“Yeah, we did it for a couple years.”
Patrick Bosworth Jul 31, 2017 ▶ 18:39
Insight
Bosworth: VC valuations shifted from prioritizing burn to balancing growth and burn
“And so, Q-three of 20 15 was just the tail end of a period when valuations of growth tech companies were inversely correlated with cash burn. The more you burned, the higher you were valued, because there was almost an exclusive focus on growth. Now it's about…”
Patrick Bosworth Jul 31, 2017 ▶ 20:45
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