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Feb 7, 2023 · 22m · top-founders

The YC of India Writes 47 Checks at $100k each for 5%, $2.5m Valuation

Nathan Latka · 9m 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 episode of Conversations with Nathan Latka, host Nathan Latka interviews Prasanna, co-founder of Indian accelerator Upekkha, to explore their flexible $100,000 investment structure, portfolio milestones, and the structural drivers fueling India's capital-efficient SaaS boom.

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 47% of the talking time here. How this is scored →

Nathan as informed peer 4.7 Guest teaching 3.7 Guest disagreement 2.7 Nathan pushing back 4.0
05100:0010:0020:000:00–2:18 · Nathan as informed peer 0/10 SaaS Open NYC Conference Announcement Solo host intro and conference advertisement outlining SaaS Open NYC and introducing guest Prasanna and Upekkha's investing terms.2:19–7:47 · Nathan as informed peer 6/10 The Structural Drivers Behind India's SaaS Expansion Prasanna contextualizes India's SaaS boom compared to the 1990s IT services expansion. Latka questions how Upekkha realizes returns from cash-flow-oriented founders who do not seek traditional exits.7:48–11:13 · Nathan as informed peer 7/10 Mechanics of the Revenue Buyback and Early-Stage Risk Latka pushes back on Upekkha using Indie.vc's terms, calling out that Indie.vc shut down and characterizing the revenue payback as expensive debt. Prasanna counters by detailing early-stage risk differentials.11:13–14:36 · Nathan as informed peer 7/10 Convertible Equity Dynamics and Venture Alignment Latka challenges the alignment of the convertible model for bootstrap-minded founders who may feel forced to raise equity or buy out. Prasanna explains how top-performing companies naturally convert to equity.14:36–17:41 · Nathan as informed peer 6/10 Evaluating Value-Add Accelerators versus Venture Studios Latka notes the tension between taking equity versus non-dilutive debt, arguing founders give up too much. Prasanna strongly defends their hands-on support, claiming they alter the company's DNA to win global customers.17:41–21:07 · Nathan as informed peer 5/10 Upekkha's Fund Structure, Portfolio Performance, and 2023 Goals Prasanna explains their AngelList rolling fund mechanics and capital deployment targets while Latka drills into fund performance, check volume, and DPI realizations.21:08–22:09 · Nathan as informed peer 2/10 Where to Find Upekkha and Final Interview Recap Quick outro where Prasanna shares upcoming events and contact channels, followed by Latka summarizing Upekkha's deal terms.0:00–2:18 · Guest teaching 0/10 SaaS Open NYC Conference Announcement Solo host intro and conference advertisement outlining SaaS Open NYC and introducing guest Prasanna and Upekkha's investing terms.2:19–7:47 · Guest teaching 5/10 The Structural Drivers Behind India's SaaS Expansion Prasanna contextualizes India's SaaS boom compared to the 1990s IT services expansion. Latka questions how Upekkha realizes returns from cash-flow-oriented founders who do not seek traditional exits.7:48–11:13 · Guest teaching 5/10 Mechanics of the Revenue Buyback and Early-Stage Risk Latka pushes back on Upekkha using Indie.vc's terms, calling out that Indie.vc shut down and characterizing the revenue payback as expensive debt. Prasanna counters by detailing early-stage risk differentials.11:13–14:36 · Guest teaching 6/10 Convertible Equity Dynamics and Venture Alignment Latka challenges the alignment of the convertible model for bootstrap-minded founders who may feel forced to raise equity or buy out. Prasanna explains how top-performing companies naturally convert to equity.14:36–17:41 · Guest teaching 7/10 Evaluating Value-Add Accelerators versus Venture Studios Latka notes the tension between taking equity versus non-dilutive debt, arguing founders give up too much. Prasanna strongly defends their hands-on support, claiming they alter the company's DNA to win global customers.17:41–21:07 · Guest teaching 3/10 Upekkha's Fund Structure, Portfolio Performance, and 2023 Goals Prasanna explains their AngelList rolling fund mechanics and capital deployment targets while Latka drills into fund performance, check volume, and DPI realizations.21:08–22:09 · Guest teaching 0/10 Where to Find Upekkha and Final Interview Recap Quick outro where Prasanna shares upcoming events and contact channels, followed by Latka summarizing Upekkha's deal terms.0:00–2:18 · Guest disagreement 0/10 SaaS Open NYC Conference Announcement Solo host intro and conference advertisement outlining SaaS Open NYC and introducing guest Prasanna and Upekkha's investing terms.2:19–7:47 · Guest disagreement 2/10 The Structural Drivers Behind India's SaaS Expansion Prasanna contextualizes India's SaaS boom compared to the 1990s IT services expansion. Latka questions how Upekkha realizes returns from cash-flow-oriented founders who do not seek traditional exits.7:48–11:13 · Guest disagreement 4/10 Mechanics of the Revenue Buyback and Early-Stage Risk Latka pushes back on Upekkha using Indie.vc's terms, calling out that Indie.vc shut down and characterizing the revenue payback as expensive debt. Prasanna counters by detailing early-stage risk differentials.11:13–14:36 · Guest disagreement 5/10 Convertible Equity Dynamics and Venture Alignment Latka challenges the alignment of the convertible model for bootstrap-minded founders who may feel forced to raise equity or buy out. Prasanna explains how top-performing companies naturally convert to equity.14:36–17:41 · Guest disagreement 6/10 Evaluating Value-Add Accelerators versus Venture Studios Latka notes the tension between taking equity versus non-dilutive debt, arguing founders give up too much. Prasanna strongly defends their hands-on support, claiming they alter the company's DNA to win global customers.17:41–21:07 · Guest disagreement 2/10 Upekkha's Fund Structure, Portfolio Performance, and 2023 Goals Prasanna explains their AngelList rolling fund mechanics and capital deployment targets while Latka drills into fund performance, check volume, and DPI realizations.21:08–22:09 · Guest disagreement 0/10 Where to Find Upekkha and Final Interview Recap Quick outro where Prasanna shares upcoming events and contact channels, followed by Latka summarizing Upekkha's deal terms.0:00–2:18 · Nathan pushing back 0/10 SaaS Open NYC Conference Announcement Solo host intro and conference advertisement outlining SaaS Open NYC and introducing guest Prasanna and Upekkha's investing terms.2:19–7:47 · Nathan pushing back 4/10 The Structural Drivers Behind India's SaaS Expansion Prasanna contextualizes India's SaaS boom compared to the 1990s IT services expansion. Latka questions how Upekkha realizes returns from cash-flow-oriented founders who do not seek traditional exits.7:48–11:13 · Nathan pushing back 7/10 Mechanics of the Revenue Buyback and Early-Stage Risk Latka pushes back on Upekkha using Indie.vc's terms, calling out that Indie.vc shut down and characterizing the revenue payback as expensive debt. Prasanna counters by detailing early-stage risk differentials.11:13–14:36 · Nathan pushing back 7/10 Convertible Equity Dynamics and Venture Alignment Latka challenges the alignment of the convertible model for bootstrap-minded founders who may feel forced to raise equity or buy out. Prasanna explains how top-performing companies naturally convert to equity.14:36–17:41 · Nathan pushing back 6/10 Evaluating Value-Add Accelerators versus Venture Studios Latka notes the tension between taking equity versus non-dilutive debt, arguing founders give up too much. Prasanna strongly defends their hands-on support, claiming they alter the company's DNA to win global customers.17:41–21:07 · Nathan pushing back 4/10 Upekkha's Fund Structure, Portfolio Performance, and 2023 Goals Prasanna explains their AngelList rolling fund mechanics and capital deployment targets while Latka drills into fund performance, check volume, and DPI realizations.21:08–22:09 · Nathan pushing back 0/10 Where to Find Upekkha and Final Interview Recap Quick outro where Prasanna shares upcoming events and contact channels, followed by Latka summarizing Upekkha's deal terms.

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

0:00 · Nathan 81.8% · guest 18.2%0:00 · Nathan 81.8% · guest 18.2%3:00 · Nathan 27.6% · guest 72.4%3:00 · Nathan 27.6% · guest 72.4%6:00 · Nathan 38.4% · guest 61.6%6:00 · Nathan 38.4% · guest 61.6%9:00 · Nathan 47.6% · guest 52.4%9:00 · Nathan 47.6% · guest 52.4%12:00 · Nathan 64.6% · guest 35.4%12:00 · Nathan 64.6% · guest 35.4%15:00 · Nathan 18.2% · guest 81.8%15:00 · Nathan 18.2% · guest 81.8%18:00 · Nathan 37.7% · guest 62.3%18:00 · Nathan 37.7% · guest 62.3%21:00 · Nathan 82.6% · guest 17.4%21:00 · Nathan 82.6% · guest 17.4%
Sharpest disagreement ▶ 15:23 Prasanna defends equity value against Latka's debt model

Prasanna forcefully challenges Latka's non-dilutive thesis, asserting that any founder would confirm Upekkha provides unique, transformative value in going global.

 Hardest push from Nathan ▶ 9:08 Latka calls out Indie.vc's failure and expensive debt structure

Latka directly confronts Prasanna on replicating the Indie.vc model by highlighting Indie.vc's shutdown and labeling the 3x revenue buyback as overly punitive debt.

 Biggest teaching moment ▶ 2:28 Prasanna contextualizes Indian software history

Prasanna educates Latka on India's historical shift from 1992 IT services to modern SaaS, explaining the deep engineering talent pool in Bangalore.

 Nathan holds their own ▶ 13:27 Latka presses on misaligned convertible terms

Latka demonstrates sharp venture capital knowledge by pressing on Indie.vc LP feedback and pointing out how forcing early buybacks penalizes cash-flowing SaaS founders.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
SaaS Open NYC Conference Announcement 0000 Solo host intro and conference advertisement outlining SaaS Open NYC and introducing guest Prasanna and Upekkha's investing terms.
The Structural Drivers Behind India's SaaS Expansion 6524 Prasanna contextualizes India's SaaS boom compared to the 1990s IT services expansion. Latka questions how Upekkha realizes returns from cash-flow-oriented founders who do not seek traditional exits.
Mechanics of the Revenue Buyback and Early-Stage Risk 7547 Latka pushes back on Upekkha using Indie.vc's terms, calling out that Indie.vc shut down and characterizing the revenue payback as expensive debt. Prasanna counters by detailing early-stage risk differentials.
Convertible Equity Dynamics and Venture Alignment 7657 Latka challenges the alignment of the convertible model for bootstrap-minded founders who may feel forced to raise equity or buy out. Prasanna explains how top-performing companies naturally convert to equity.
Evaluating Value-Add Accelerators versus Venture Studios 6766 Latka notes the tension between taking equity versus non-dilutive debt, arguing founders give up too much. Prasanna strongly defends their hands-on support, claiming they alter the company's DNA to win global customers.
Upekkha's Fund Structure, Portfolio Performance, and 2023 Goals 5324 Prasanna explains their AngelList rolling fund mechanics and capital deployment targets while Latka drills into fund performance, check volume, and DPI realizations.
Where to Find Upekkha and Final Interview Recap 2000 Quick outro where Prasanna shares upcoming events and contact channels, followed by Latka summarizing Upekkha's deal terms.

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