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Dec 24, 2016 · 20m · top-founders

EP 518: See 20 deals, invest in 2 between $75k-150k pre seed, likes b2b saas for investments

Dinesh Kandanchatha · 9m spoken Nathan Latka · 8m spoken
0:00 / 0:00

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In this episode of "The Top," host Nathan Latka interviews serial entrepreneur and angel investor Dinesh Kandanchatha to explore his hands-on pre-seed B2B SaaS investment strategy, board governance economics, and high-stakes venture experiences. Dinesh shares lessons from surviving severe startup setbacks to scaling Protus IP Solutions to an $80 million ARR turnaround and subsequent $213 million acquisition.

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 45.9% of the talking time here. How this is scored →

Nathan as informed peer 4.1 Guest teaching 2.4 Guest disagreement 0.9 Nathan pushing back 1.9
05100:0010:0020:000:28–3:04 · Nathan as informed peer 4/10 Weekly Giveaway Winner Announcement and Subscription Guidelines Nathan introduces Dinesh and immediately pushes to narrow down his multifaceted bio into a clear single business focus. Dinesh answers cleanly and sets up the conversation.3:04–5:25 · Nathan as informed peer 5/10 Corporate Board Compensation and Value Creation Mechanics Nathan explores board seat compensation and accredited investor criteria, while Dinesh breaks down the math of board retainers requiring 10-20x value generation.5:26–8:57 · Nathan as informed peer 4/10 Hands-On Pre-Seed Angel Investment Strategy and Acceleration Dinesh outlines his pre-seed investment model and recounts being sued by a past acquirer, explaining that being legally right does not protect a startup from financial devastation.8:57–11:26 · Nathan as informed peer 5/10 Scaling Protus IP Solutions to Eighty Million ARR Nathan quickly catches and clarifies Dinesh's slip when discussing eighty million ARR versus monthly revenue, keeping the financial metrics precise.11:26–14:55 · Nathan as informed peer 5/10 Protus Acquisition by J2 Global and Risk Realities Nathan calculates Dinesh's potential exit payout based on public records and equity share, while Dinesh explains his investment philosophy and active role in Patriot One Technologies.14:55–17:23 · Nathan as informed peer 2/10 Connecting Online and Charity Mentorship via Clarity Dinesh mentions his Clarity.fm profile where all advisory fees go to charity, followed by Nathan running mid-roll promo monologues.17:24–19:04 · Nathan as informed peer 4/10 The Famous Five Rapid-Fire Questions with Dinesh Nathan runs through the Famous Five rapid-fire questions, drawing out Dinesh's lessons about networking and not aiming to be the smartest person in the room.0:28–3:04 · Guest teaching 0/10 Weekly Giveaway Winner Announcement and Subscription Guidelines Nathan introduces Dinesh and immediately pushes to narrow down his multifaceted bio into a clear single business focus. Dinesh answers cleanly and sets up the conversation.3:04–5:25 · Guest teaching 5/10 Corporate Board Compensation and Value Creation Mechanics Nathan explores board seat compensation and accredited investor criteria, while Dinesh breaks down the math of board retainers requiring 10-20x value generation.5:26–8:57 · Guest teaching 3/10 Hands-On Pre-Seed Angel Investment Strategy and Acceleration Dinesh outlines his pre-seed investment model and recounts being sued by a past acquirer, explaining that being legally right does not protect a startup from financial devastation.8:57–11:26 · Guest teaching 3/10 Scaling Protus IP Solutions to Eighty Million ARR Nathan quickly catches and clarifies Dinesh's slip when discussing eighty million ARR versus monthly revenue, keeping the financial metrics precise.11:26–14:55 · Guest teaching 3/10 Protus Acquisition by J2 Global and Risk Realities Nathan calculates Dinesh's potential exit payout based on public records and equity share, while Dinesh explains his investment philosophy and active role in Patriot One Technologies.14:55–17:23 · Guest teaching 1/10 Connecting Online and Charity Mentorship via Clarity Dinesh mentions his Clarity.fm profile where all advisory fees go to charity, followed by Nathan running mid-roll promo monologues.17:24–19:04 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions with Dinesh Nathan runs through the Famous Five rapid-fire questions, drawing out Dinesh's lessons about networking and not aiming to be the smartest person in the room.0:28–3:04 · Guest disagreement 1/10 Weekly Giveaway Winner Announcement and Subscription Guidelines Nathan introduces Dinesh and immediately pushes to narrow down his multifaceted bio into a clear single business focus. Dinesh answers cleanly and sets up the conversation.3:04–5:25 · Guest disagreement 1/10 Corporate Board Compensation and Value Creation Mechanics Nathan explores board seat compensation and accredited investor criteria, while Dinesh breaks down the math of board retainers requiring 10-20x value generation.5:26–8:57 · Guest disagreement 2/10 Hands-On Pre-Seed Angel Investment Strategy and Acceleration Dinesh outlines his pre-seed investment model and recounts being sued by a past acquirer, explaining that being legally right does not protect a startup from financial devastation.8:57–11:26 · Guest disagreement 1/10 Scaling Protus IP Solutions to Eighty Million ARR Nathan quickly catches and clarifies Dinesh's slip when discussing eighty million ARR versus monthly revenue, keeping the financial metrics precise.11:26–14:55 · Guest disagreement 1/10 Protus Acquisition by J2 Global and Risk Realities Nathan calculates Dinesh's potential exit payout based on public records and equity share, while Dinesh explains his investment philosophy and active role in Patriot One Technologies.14:55–17:23 · Guest disagreement 0/10 Connecting Online and Charity Mentorship via Clarity Dinesh mentions his Clarity.fm profile where all advisory fees go to charity, followed by Nathan running mid-roll promo monologues.17:24–19:04 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions with Dinesh Nathan runs through the Famous Five rapid-fire questions, drawing out Dinesh's lessons about networking and not aiming to be the smartest person in the room.0:28–3:04 · Nathan pushing back 2/10 Weekly Giveaway Winner Announcement and Subscription Guidelines Nathan introduces Dinesh and immediately pushes to narrow down his multifaceted bio into a clear single business focus. Dinesh answers cleanly and sets up the conversation.3:04–5:25 · Nathan pushing back 2/10 Corporate Board Compensation and Value Creation Mechanics Nathan explores board seat compensation and accredited investor criteria, while Dinesh breaks down the math of board retainers requiring 10-20x value generation.5:26–8:57 · Nathan pushing back 3/10 Hands-On Pre-Seed Angel Investment Strategy and Acceleration Dinesh outlines his pre-seed investment model and recounts being sued by a past acquirer, explaining that being legally right does not protect a startup from financial devastation.8:57–11:26 · Nathan pushing back 3/10 Scaling Protus IP Solutions to Eighty Million ARR Nathan quickly catches and clarifies Dinesh's slip when discussing eighty million ARR versus monthly revenue, keeping the financial metrics precise.11:26–14:55 · Nathan pushing back 2/10 Protus Acquisition by J2 Global and Risk Realities Nathan calculates Dinesh's potential exit payout based on public records and equity share, while Dinesh explains his investment philosophy and active role in Patriot One Technologies.14:55–17:23 · Nathan pushing back 0/10 Connecting Online and Charity Mentorship via Clarity Dinesh mentions his Clarity.fm profile where all advisory fees go to charity, followed by Nathan running mid-roll promo monologues.17:24–19:04 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions with Dinesh Nathan runs through the Famous Five rapid-fire questions, drawing out Dinesh's lessons about networking and not aiming to be the smartest person in the room.

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

0:00 · Nathan 78.8% · guest 21.2%0:00 · Nathan 78.8% · guest 21.2%3:00 · Nathan 28.9% · guest 71.1%3:00 · Nathan 28.9% · guest 71.1%6:00 · Nathan 17.5% · guest 82.5%6:00 · Nathan 17.5% · guest 82.5%9:00 · Nathan 27.1% · guest 72.9%9:00 · Nathan 27.1% · guest 72.9%12:00 · Nathan 18.3% · guest 81.7%12:00 · Nathan 18.3% · guest 81.7%15:00 · Nathan 75.3% · guest 24.7%15:00 · Nathan 75.3% · guest 24.7%18:00 · Nathan 89% · guest 11%18:00 · Nathan 89% · guest 11%
Sharpest disagreement ▶ 8:00 Dinesh challenges the premise of winning startup lawsuits

Dinesh pushes back on whether he won his legal battle, pointing out that whether you are right or wrong, prolonged litigation drains resources and kills the venture.

 Hardest push from Nathan ▶ 2:14 Nathan challenges vague guest introduction

Nathan cuts through the broad introduction to insist that Dinesh state his singular, primary commercial focus so listeners understand how he operates.

 Biggest teaching moment ▶ 3:43 Dinesh explains board seat ROI expectations

Dinesh educates Nathan on private board compensation mechanics, detailing how board members must generate 10 to 20 times their retainer and equity in direct value.

 Nathan holds their own ▶ 10:09 Nathan catches and corrects ARR and MRR confusion

Nathan intervenes immediately when Dinesh mentions eighty million monthly revenue, correcting the metric to annual recurring revenue and calculating the corresponding monthly run rate.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Weekly Giveaway Winner Announcement and Subscription Guidelines 4012 Nathan introduces Dinesh and immediately pushes to narrow down his multifaceted bio into a clear single business focus. Dinesh answers cleanly and sets up the conversation.
Corporate Board Compensation and Value Creation Mechanics 5512 Nathan explores board seat compensation and accredited investor criteria, while Dinesh breaks down the math of board retainers requiring 10-20x value generation.
Hands-On Pre-Seed Angel Investment Strategy and Acceleration 4323 Dinesh outlines his pre-seed investment model and recounts being sued by a past acquirer, explaining that being legally right does not protect a startup from financial devastation.
Scaling Protus IP Solutions to Eighty Million ARR 5313 Nathan quickly catches and clarifies Dinesh's slip when discussing eighty million ARR versus monthly revenue, keeping the financial metrics precise.
Protus Acquisition by J2 Global and Risk Realities 5312 Nathan calculates Dinesh's potential exit payout based on public records and equity share, while Dinesh explains his investment philosophy and active role in Patriot One Technologies.
Connecting Online and Charity Mentorship via Clarity 2100 Dinesh mentions his Clarity.fm profile where all advisory fees go to charity, followed by Nathan running mid-roll promo monologues.
The Famous Five Rapid-Fire Questions with Dinesh 4201 Nathan runs through the Famous Five rapid-fire questions, drawing out Dinesh's lessons about networking and not aiming to be the smartest person in the room.

Statements from this episode (10)

Insight
Kandanchatha charges advisory fees so founders value his advice
“I also, you know, do some consulting work and board work. But that's mostly just that's just mostly to support the entrepreneurs and, you know, put, Put a dollar beside it so that people don't ignore what I say.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 2:50
Insight
Board members must generate 10x to 20x their pay in value
“Whatever you're getting paid, you have to generate 10 to 20 times that in value. Otherwise you won't keep your seat. So if you can't, if you're getting paid a thousand bucks a month, you better be able to generate Like 20,000 dollars in either cost savings or …”
Dinesh Kandanchatha Dec 24, 2016 ▶ 3:49
Disclosure
Kandanchatha sees 20 deals a year and invests in two
“I probably see around 20 deals a year, of which I would invest in two and a bunch of the other ones I continue to advise.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 5:52
Disclosure
Kandanchatha writes angel checks between $75k and $150k
“Between 75 and 150 K, depending on what's there, and you know, it's small money, I guess, in some ways.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 6:04
Disclosure
Kandanchatha works one day weekly with his pre-seed portfolio companies
“I'm pre-Series A, often pre-seed, and what I'm trying to do there is Take my capital and amplify it with my network and my experience. So you need to take 75 K Worth of capital, but then I'm working with you. I'm putting a day into your business and a day a we…”
Dinesh Kandanchatha Dec 24, 2016 ▶ 6:15
Insight
Startup lawsuits sideline founders regardless of who is legally right
“Well, it's the funny thing I learned about that process is it doesn't matter if you're right or wrong. No, totally. It just puts you on the sidelines”
Dinesh Kandanchatha Dec 24, 2016 ▶ 8:00
Assertion Not checkable as stated
Kandanchatha spent hundreds of thousands defending an early startup lawsuit
“I ended up spending hundreds of thousands of dollars in legal battles instead of building my company”
Dinesh Kandanchatha Dec 24, 2016 ▶ 8:06
Assertion Supported
Protus IP Solutions grew from near zero to $80M ARR in six years
“And so it, coming in and then working with the founders and then building out a sales and marketing organization and then taking the revenue to basically zero and then growing it all the way back up to eighty million dollars in software as a service.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 9:53
Disclosure
Kandanchatha targets 3% to 5% equity stakes for 10x returns
“And that's kind of my thing is I kind of get in at the three, four, five percent Level. And then, you know, help really scale that up to through those three things, capital, network, and expertise to turn, you know, get a 10 X return.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 11:09
Prediction Open · timeframe Dec 2019
Kandanchatha predicts Patriot One Technologies will become a billion-dollar company
“And I want to make sure that I'm, that it's going to get executed effectively and it's going to be a billion dollar company.”
Dinesh Kandanchatha Dec 24, 2016 ▶ 14:50
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