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Aug 3, 2015 · 29m · 20vc

20 VC 059: How To Approach VCs with Arteen Arabshahi, VC @ Karlin Ventures

Arteen Arabshahi · 22m spoken Harry Stebbings · 5m spoken
0:00 / 0:00

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In episode 059 of The 20 Minute VC, host Harry Stebbings speaks with Karlin Ventures VC Arteen Arabshahi about cold outreach strategies, marketplace investment theses, and founder mental health. The conversation delivers practical insights for early-stage entrepreneurs on securing venture funding and navigating startup pressures.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 18.1% of the talking time here. How this is scored →

Harry as informed peer 2.4 Guest teaching 3.0 Guest disagreement 1.0 Harry pushing back 1.4
05100:0010:0020:001:24–11:25 · Harry as informed peer 2/10 Arteen's Background & Path to Venture Capital Harry asks standard biographical questions and prompts Arteen on whether there is a fixed traditional route into venture capital. Arteen explains his non-traditional transition from pre-med to Techstars and Karlin Ventures while Harry offers warm agreement.11:25–15:12 · Harry as informed peer 3/10 Cold Outreach Strategies & Finding Contact Info Harry and Arteen exchange practical cold email advice. Harry shares his real-time experience emailing Brad Feld, while Arteen details useful outreach tactics and tools like Reportive.15:12–20:24 · Harry as informed peer 2/10 Marketplace Investment Thesis at Karlin Ventures When Harry asks for a specific market size metric that excites him, Arteen reframes the prompt by explaining that investor decisions on market size are largely visceral and binary.20:24–26:00 · Harry as informed peer 3/10 Managing Founder Mental Health and Self-Doubt Arteen candidly shares his personal experiences with depression, self-doubt, and mental health non-profits. Harry actively contributes by recommending mindfulness tools like Headspace.26:00–28:27 · Harry as informed peer 2/10 Quick Fire Round During the quick fire round, Arteen provides crisp insights on investment red flags, favorite media sources, and recent deals like PolicyGenius.1:24–11:25 · Guest teaching 3/10 Arteen's Background & Path to Venture Capital Harry asks standard biographical questions and prompts Arteen on whether there is a fixed traditional route into venture capital. Arteen explains his non-traditional transition from pre-med to Techstars and Karlin Ventures while Harry offers warm agreement.11:25–15:12 · Guest teaching 3/10 Cold Outreach Strategies & Finding Contact Info Harry and Arteen exchange practical cold email advice. Harry shares his real-time experience emailing Brad Feld, while Arteen details useful outreach tactics and tools like Reportive.15:12–20:24 · Guest teaching 4/10 Marketplace Investment Thesis at Karlin Ventures When Harry asks for a specific market size metric that excites him, Arteen reframes the prompt by explaining that investor decisions on market size are largely visceral and binary.20:24–26:00 · Guest teaching 2/10 Managing Founder Mental Health and Self-Doubt Arteen candidly shares his personal experiences with depression, self-doubt, and mental health non-profits. Harry actively contributes by recommending mindfulness tools like Headspace.26:00–28:27 · Guest teaching 3/10 Quick Fire Round During the quick fire round, Arteen provides crisp insights on investment red flags, favorite media sources, and recent deals like PolicyGenius.1:24–11:25 · Guest disagreement 1/10 Arteen's Background & Path to Venture Capital Harry asks standard biographical questions and prompts Arteen on whether there is a fixed traditional route into venture capital. Arteen explains his non-traditional transition from pre-med to Techstars and Karlin Ventures while Harry offers warm agreement.11:25–15:12 · Guest disagreement 1/10 Cold Outreach Strategies & Finding Contact Info Harry and Arteen exchange practical cold email advice. Harry shares his real-time experience emailing Brad Feld, while Arteen details useful outreach tactics and tools like Reportive.15:12–20:24 · Guest disagreement 2/10 Marketplace Investment Thesis at Karlin Ventures When Harry asks for a specific market size metric that excites him, Arteen reframes the prompt by explaining that investor decisions on market size are largely visceral and binary.20:24–26:00 · Guest disagreement 0/10 Managing Founder Mental Health and Self-Doubt Arteen candidly shares his personal experiences with depression, self-doubt, and mental health non-profits. Harry actively contributes by recommending mindfulness tools like Headspace.26:00–28:27 · Guest disagreement 1/10 Quick Fire Round During the quick fire round, Arteen provides crisp insights on investment red flags, favorite media sources, and recent deals like PolicyGenius.1:24–11:25 · Harry pushing back 2/10 Arteen's Background & Path to Venture Capital Harry asks standard biographical questions and prompts Arteen on whether there is a fixed traditional route into venture capital. Arteen explains his non-traditional transition from pre-med to Techstars and Karlin Ventures while Harry offers warm agreement.11:25–15:12 · Harry pushing back 1/10 Cold Outreach Strategies & Finding Contact Info Harry and Arteen exchange practical cold email advice. Harry shares his real-time experience emailing Brad Feld, while Arteen details useful outreach tactics and tools like Reportive.15:12–20:24 · Harry pushing back 2/10 Marketplace Investment Thesis at Karlin Ventures When Harry asks for a specific market size metric that excites him, Arteen reframes the prompt by explaining that investor decisions on market size are largely visceral and binary.20:24–26:00 · Harry pushing back 1/10 Managing Founder Mental Health and Self-Doubt Arteen candidly shares his personal experiences with depression, self-doubt, and mental health non-profits. Harry actively contributes by recommending mindfulness tools like Headspace.26:00–28:27 · Harry pushing back 1/10 Quick Fire Round During the quick fire round, Arteen provides crisp insights on investment red flags, favorite media sources, and recent deals like PolicyGenius.

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

0:00 · Harry 60.6% · guest 39.4%0:00 · Harry 60.6% · guest 39.4%3:00 · Harry 4.5% · guest 95.5%3:00 · Harry 4.5% · guest 95.5%6:00 · Harry 3.4% · guest 96.6%6:00 · Harry 3.4% · guest 96.6%9:00 · Harry 14.5% · guest 85.5%9:00 · Harry 14.5% · guest 85.5%12:00 · Harry 8% · guest 92%12:00 · Harry 8% · guest 92%15:00 · Harry 9.6% · guest 90.4%15:00 · Harry 9.6% · guest 90.4%18:00 · Harry 20.8% · guest 79.2%18:00 · Harry 20.8% · guest 79.2%21:00 · Harry 0% · guest 100%21:00 · Harry 0% · guest 100%24:00 · Harry 12.3% · guest 87.7%24:00 · Harry 12.3% · guest 87.7%27:00 · Harry 51% · guest 49%27:00 · Harry 51% · guest 49%
Sharpest disagreement ▶ 18:46 Softly challenging the premise of market sizing

Arteen gently rejects Harry's attempt to quantify required market size, stating that if a founder has to convince an investor the market is big enough, the deal won't happen.

 Hardest push from Harry ▶ 9:52 Challenging the standard VC entry thesis

Harry asks Arteen whether he agrees or disagrees with the common belief that banking, consulting, or founding a startup are the only real entry paths into VC.

 Biggest teaching moment ▶ 26:24 Defining founder domain expertise standard

Arteen articulates a firm rule that if he knows more about a sector than the pitching founder, it is an automatic rejection because founders must know 120% of their domain.

 Harry holds his own ▶ 12:43 Demonstrating active networking speed

Harry steps in with his own proof point about email etiquette, noting he emailed Brad Feld 15 minutes prior and got a reply within 3 minutes.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Arteen's Background & Path to Venture Capital 2312 Harry asks standard biographical questions and prompts Arteen on whether there is a fixed traditional route into venture capital. Arteen explains his non-traditional transition from pre-med to Techstars and Karlin Ventures while Harry offers warm agreement.
Cold Outreach Strategies & Finding Contact Info 3311 Harry and Arteen exchange practical cold email advice. Harry shares his real-time experience emailing Brad Feld, while Arteen details useful outreach tactics and tools like Reportive.
Marketplace Investment Thesis at Karlin Ventures 2422 When Harry asks for a specific market size metric that excites him, Arteen reframes the prompt by explaining that investor decisions on market size are largely visceral and binary.
Managing Founder Mental Health and Self-Doubt 3201 Arteen candidly shares his personal experiences with depression, self-doubt, and mental health non-profits. Harry actively contributes by recommending mindfulness tools like Headspace.
Quick Fire Round 2311 During the quick fire round, Arteen provides crisp insights on investment red flags, favorite media sources, and recent deals like PolicyGenius.

Statements from this episode (9)

Opinion
Stebbings: The tech industry is entirely a meritocracy above any other
“I think that's the beauty of the tech industry above any other. It's entirely a meritocracy.”
Harry Stebbings Aug 3, 2015 ▶ 7:18
Disclosure
Karlin Ventures has a $60 million allocation for a five-year fund
“We have sixty million an allocation and it's a five year fund.”
Arteen Arabshahi Aug 3, 2015 ▶ 8:55
Opinion
Arabshahi: Brad Feld has exceptional email response etiquette and speed
“Brad, Brad is like, I mean, the guy, his email response etiquette and ratio is just like tremendous.”
Arteen Arabshahi Aug 3, 2015 ▶ 12:29
Disclosure
Karlin Ventures invests $250K to $1.5M in enterprise software and marketplaces
“Our focus is mostly enterprise software and marketplaces. We, we've done a few other things, some ad tech, some commerce platforms and things like that. But really enterprise and marketplaces are the core focus and typically investing between two 50 K up to ab…”
Arteen Arabshahi Aug 3, 2015 ▶ 15:27
Opinion
Arabshahi: Most horizontal marketplace opportunities have already been captured
“Most horizontal infrastructure that is going to be disrupted by big marketplaces has probably already been done so, right? So like Uber Airbnb, like the, you know, I think taxis are pretty much taken care of at this point.”
Arteen Arabshahi Aug 3, 2015 ▶ 17:00
Insight
Arabshahi: VCs pass if founders must convince them the market is big
“If you have to convince an investor how, like, that the market is big enough, they're probably not going to do it is kind of my notion.”
Arteen Arabshahi Aug 3, 2015 ▶ 19:00
Insight
Arabshahi: Karlin Ventures passes if founders know less than the investors
“If I feel like I know more about the sector than the entrepreneur does, there's no way we'll invest, because I probably have a 60 to 70% understanding of a lot of things, but if you're starting a company in that space, you should know a 120% of it.”
Arteen Arabshahi Aug 3, 2015 ▶ 26:30
Disclosure
Karlin Ventures invested in the Series A for insurance marketplace Policygenius
“We did an investment out of New York called Policy Genius. We did a Series A, and it's a marketplace for life, rent, pet, and disability insurance.”
Arteen Arabshahi Aug 3, 2015 ▶ 27:56
Insight
Arabshahi: Industry expertise and customer acquisition are insurance marketplaces' hardest challenges
“One of the founders has, like, incredibly relevant industry expertise, and the other one has amazing expertise in customer acquisition, and I think those are probably the Two hardest things that a marketplace for insurance will face.”
Arteen Arabshahi Aug 3, 2015 ▶ 28:14
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