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



In this episode of the 20 minutes VC, host Harry Stebbings interviews venture capitalist Artin Arab Shahi of Carlin Ventures, exploring his unconventional journey from aspiring plastic surgeon to VC, through pivotal experiences at accelerate Labs (now Techstars Chicago) and Built in LA. Artin shares insights on the art of cold emailing influential figures, the excitement surrounding marketplaces and enterprise software, and the importance of market size in investment decisions. He also touches on the personal challenges of entrepreneurship, discussing mental health and tools like Headspace that can aid in maintaining well-being. Artin's emphasis on meritocracy in the tech industry and his approach to venture capital, which includes a focus on disrupting antiquated industries through marketplaces and supporting infrastructure, are highlighted. The episode concludes with Artin's thoughts on the importance of founder expertise and his latest investment in Policy Genius, a marketplace for various insurances.

Summary Notes

Introduction to Artin Arabshahi and Carlin Ventures

  • Artin Arabshahi is a venture capitalist at Carlin Ventures with a focus on enterprise software, commerce, platforms, and marketplaces.
  • Before joining Carlin Ventures, Artin launched Built in LA, a community for digital entrepreneurs and innovators.
  • Artin's startup experience includes operations at Accelerate Labs, now known as Techstars Chicago.

"Artin is a VC at Carlin Ventures where he specializes in enterprise software, commerce, platforms and marketplaces." "Prior to Carlin Ventures, Artin spearheaded the launch of Built in LA, an online community for digital entrepreneurs and innovators." "However, his passion for startups flourished while helping run operations at accelerate Labs, now techstars Chicago."

These quotes outline Artin Arabshahi's current role and his background experience, highlighting his focus areas in venture capital and his previous entrepreneurial endeavors.

Artin's Unique Path to Venture Capital

  • Artin's journey into VC was not traditional, and he entered the field somewhat haphazardly.
  • Originally from Tucson, Arizona, Artin grew up with the ambition to become a plastic surgeon.
  • He started college in the Bay Area, pre-med, but transferred back to Arizona for a double major in finance and entrepreneurship, eventually dropping the pre-med track.

"I think I actually have a bit of a unique path to venture." "I spent the majority of my life thinking I was going to be a plastic surgeon."

The quotes reflect Artin's initial career aspirations and his non-traditional path into the venture capital world, emphasizing the shift from a medical career to one in finance and entrepreneurship.

Transition from Plastic Surgery to Entrepreneurship

  • Artin's decision to leave medicine was driven by his entrepreneurial spirit and the realization that he did not want to start his career in his mid-to-late thirties.
  • He had always been involved in starting small businesses and wanted to retain a business aspect in his career.
  • After abandoning his plan to become a plastic surgeon, Artin interned in investment banking in New York, which led to his interest in tech and startups.

"After a couple of years of premed was when I really realized I couldn't fathom starting my career as a surgeon when I was like in my mid to late thirty s." "I wanted to have a business side to whatever I did."

The quotes capture Artin's reasoning behind his career change and his desire to combine business with his professional pursuits, ultimately leading him away from medicine and towards entrepreneurship and venture capital.

Breaking into Tech and VC with No Contacts

  • Artin had no existing contacts in tech or VC but was determined to break into the field.
  • He created a list of 150 people in the tech community he wanted to work for and sent out personalized cold emails.
  • His scrappy approach paid off, with some recipients taking a chance on him based on his cold emails.

"I made a list of about 150 people that I wanted to work for." "Literally none. Yeah, I got really lucky that I had some people take a chance on me off of a cold email."

These quotes highlight Artin's proactive and resourceful methods for networking and gaining entry into the tech and VC communities, despite having no initial contacts.

Artin's Cold Email Strategy

  • Artin's cold emails were concise and to the point, with personalized touches when appropriate.
  • He offered to work for free and presented his relevant background succinctly.
  • The response to his emails was positive, leading to interviews and ultimately a position with Techstars Chicago.

"It was about 150 emails. I would say probably 20 or 30 of them were very personalized where it was like, okay, I know this person's story." "Do you have any opportunities for an undergrad this coming summer? And I'll work for free."

These quotes describe the strategic approach Artin took when reaching out to potential employers through cold emails, emphasizing personalization and a willingness to gain experience without immediate compensation.

Experience at Techstars Chicago

  • At Techstars Chicago, Artin was part of the operations team and engaged in various tasks from financial modeling to planning demo days.
  • The Techstars experience was pivotal for Artin, as it was his first deep foray into the startup world.
  • He valued the meritocratic nature of the tech industry, where age and background are less important than ideas and hard work.

"The Techstars experience was definitely my first deep foray into this world." "Nobody really cares how old or how young you are or what your background is, but if you're bringing good ideas to the table, you're presenting them well and you're working hard and you're doing a good job that gets rewarded."

These quotes reflect on Artin's hands-on experience at Techstars Chicago and the meritocratic culture he appreciated, which recognized and rewarded hard work and good ideas regardless of one's background.

Launching Built in LA

  • After Techstars, Artin helped launch Built in LA, an online community for the tech ecosystem in Los Angeles.
  • His move to LA was facilitated by his work with Built in Chicago and the opportunity to replicate the community model in a new city.

"And after tech stars, I actually became pretty close with a company out in Chicago called built in Chicago, which is like an online community for the tech ecosystem." "And they were looking to launch built in LA."

The quotes explain Artin's involvement with the expansion of the Built in community from Chicago to Los Angeles, highlighting his role in fostering local tech ecosystems.

Artin Arabshahi's Journey to Venture Capital (VC)

  • Artin Arabshahi moved to Los Angeles (LA) in 2012, drawn by the growing tech ecosystem.
  • He met his current partner at Carlin Ventures during a Techstars demo day.
  • Their relationship evolved over coffee meetings and discussions about the industry.
  • Artin joined Carlin Ventures in 2013, early in the fund's life, which had started in August 2012 with a five-year, $60 million allocation.
  • He acknowledges his unconventional path into VC, without the ambition to do so from the start.
  • Artin believes his career will oscillate between operating and VC roles, with a constant love for the tech industry.

This was in 2012 when the ecosystem out here had just kind of really hit an inflection point where it was clear that this wasn't going away and there was a ton of growth and I wanted to be a part of it.

This quote explains Artin's motivation to move to LA, influenced by the significant growth and stability of the tech ecosystem at that time.

And so I was fortunate in that TX, my partner definitely took a chance on me. And on the flip side, I was also taking a chance on him in the sense that it was a new fund.

Artin acknowledges the mutual risk involved in joining an early-stage VC fund and the opportunity it presented for both him and his partner.

The Conventional Path into VC

  • Artin considers himself an anomaly to the typical VC entry path of investment banking, consultancy, or being a startup founder.
  • He estimates that about 80% of VC entrants follow this formula, though he made up the percentage.
  • Artin believes that while the conventional path can open doors, having a unique background can also be an "X factor."
  • He admits that his different experiences have resulted in both strengths and weaknesses compared to peers with more traditional backgrounds.

Regardless of my opinion, I think it's definitely I'm anomaly in the sense that I'm a proven disagreement with that, but I think that that's the status quo.

Artin acknowledges that his path into VC is not the norm, indicating that there is a standard expectation of how one enters the VC field.

So I would say that that formula definitely helps get you in the door, but there's also a lot of people who come with that background, so there has to be something on top of that.

This quote suggests that while a traditional background is helpful for entering VC, it is not the only factor, and having additional unique qualities can be beneficial.

Personalized Communication in Professional Outreach

  • Artin experimented with personalized emails to top-tier individuals, which were time-consuming but potentially more effective.
  • He found his conversion rate for responses was about equal between personalized and less personal emails.
  • Artin credits Troy from Techstars Chicago and Brad Feld for their roles in his professional development.
  • Brad Feld, in particular, impressed Artin with his responsiveness and accessibility via email.
  • Artin chose an opportunity with Accelerate Labs over Techstars Boulder, which later merged with Techstars Chicago.

So I think my experiment had too many variables. So the reason, I mean, that is that the people that I sent the personalized emails to were actually usually the hardest people to reach.

Artin reflects on the complexity of his approach to outreach and acknowledges that the high-profile nature of the recipients may have skewed his results.

Yeah, it's tremendous. And I was literally some random kid emailing him from the University of Arizona with almost no relevant background. And he replied and gave me all the right people to talk to at I.

Artin expresses gratitude for Brad Feld's willingness to engage with him despite his lack of experience, illustrating the value of accessibility in professional networks.

Obtaining Contact Information for Networking

  • Artin did not use special tools to find email addresses of top-tier VCs, relying instead on common patterns and web research.
  • He suggests using tools like the Gmail plugin Reportive to verify email addresses.
  • Artin advises against sending emails to generic "info" addresses of VC funds, as they are less likely to yield responses.

Yeah, no, I mean, it was all just me kind of looking around. I think these days it's not that hard to find people's email addresses right at the end of the day, like, I think probably, you know, 80% to 90% of people, it's just their first name at the domain, right? Or it's their first name initial and their last name.

Artin explains his straightforward method for finding email addresses and suggests that most can be guessed based on common email address structures.

I'm not like an investor or anything. I just love the fact that you can plug in an email and you can automatically know if it's right because if they pull up the person's LinkedIn and social profiles and things like that, you know that the email address is correct.

He endorses the usefulness of the Reportive plugin as a verification tool for ensuring the accuracy of email addresses during outreach efforts.

Initial Outreach to Carlin Ventures

  • Artin Arabshahi reached out to Carlin Ventures via a general email address.
  • The method used for contact might not yield the best response rate.

Yeah, exactly. Not the best response ratio.

These quotes indicate that Artin used a basic contact method to reach out to Carlin Ventures, which he acknowledges may not be the most effective way to get a response.

Focus and Excitement about Marketplaces

  • Carlin Ventures primarily focuses on enterprise software and marketplaces.
  • The firm also invests in ad tech and commerce platforms.
  • Investment size ranges from $250k to $1.5 million, targeting late seed to early series A stages.
  • Marketplaces are favored for their potential to disrupt old and antiquated industries.
  • The firm appreciates improvements in efficiency, process, and experience within industries.

Yeah, absolutely. So just the quick high level on Carlin Ventures in general, our focus is mostly enterprise software and marketplaces... But really enterprise and marketplaces are the core focus. ...we just love to see old kind of antiquated industries get disrupted.

Artin explains Carlin Ventures' investment focus and their enthusiasm for marketplaces, especially those that modernize outdated sectors.

Vertically Specific Marketplaces and Marketplace Infrastructure

  • Carlin Ventures is interested in vertically specific marketplaces.
  • They believe most horizontal infrastructure disruptions have already occurred.
  • Vertically specific marketplaces can have higher conversion ratios and average order values.
  • The firm has invested in a company called Laurel and Wolf, an interior design marketplace.
  • They also invest in marketplace infrastructure to enhance efficiency.
  • An example is Shiphawk, which optimizes shipping for various marketplaces.

And so one of them is vertically specific marketplaces... I think that markets like that, while maybe the total market size isn't quite as large... ...what we call marketplace infrastructure. So tools that help marketplaces be more efficient and more effective.

Artin discusses Carlin Ventures' two main areas of interest: niche marketplaces tailored to specific verticals and tools that support the operational efficiency of marketplaces.

Market Size Considerations for Investment

  • The market size must be inherently convincing to investors.
  • Carlin Ventures looks for markets that are growing and already significant in size.
  • Artin suggests that investors' perceptions of market size are often instinctual and difficult to change with data alone.

That's a good question, but it's probably not when I have a good answer for it... if you have to convince an investor that the market is big enough, they're probably not going to do it is kind of my notion.

Artin conveys that the appeal of a market's size is more intuitive than analytical, implying that investors should be naturally convinced of a market's potential without needing persuasion.

Entrepreneurial Self-Doubt and Coping Mechanisms

  • Self-doubt is a common experience among entrepreneurs.
  • Coping with self-doubt is a personal journey, and strategies differ from person to person.
  • Artin shares his own experience with self-doubt during college.
  • He overcame challenges by dedicating himself to productive endeavors.

I think that when it comes to this topic, just in general, I think there's a couple of caveats that I always like to start with, right... I think the most important part about this is figuring out for yourself what exactly it is that helps keep you going. ...what made me get better, to be honest, and what made me feel better was actually throwing it all towards something that I thought was productive.

Artin emphasizes the individual nature of dealing with self-doubt and shares his personal approach, which involved focusing on productive activities to overcome feelings of insignificance.

Overcoming Self-Doubt and Mental Health Struggles

  • Artin Arabshahi shares his personal strategy for coping with self-doubt by maintaining a regimented and productive routine.
  • He emphasizes the importance of being aware of one's mental health and finding individual solutions.
  • Artin advocates for mental health awareness and subtly integrating it into daily life.
  • He mentions his support for the nonprofit 'To Write Love on Her Arms' which aids those struggling with mental health and addiction.

I sent all of those emails while I was in probably the worst month or two of the self doubt that I was going through.

This quote highlights the period when Artin was struggling with self-doubt and how he managed to remain productive despite the challenges.

And so for me, that was the way I was able to kind of overcome it, and it worked.

Artin describes his personal method of overcoming self-doubt, suggesting that while it worked for him, it may not be universal.

I consistently am questioning things about happiness. Right. So it's like now my thoughts are more around, like, okay, am I really happy?

Artin shares his ongoing contemplation about happiness, indicating a continuous self-evaluation of his mental well-being.

I'm still a huge fan of and a volunteer for is a nonprofit called to write Love on our arms.

He expresses his involvement with a nonprofit that supports mental health, highlighting the importance of such organizations in his life.

Mental Health Tools and Practices

  • Artin discusses the value of mental health tools, though he personally has not used apps like Headspace or Calm.
  • He mentions an interest in breathing exercises and the potential benefits of yoga for mental health.
  • Artin stresses that different methods work for different people and promotes a holistic approach to happiness and health.

So I haven't myself. I have a lot of friends who have, though, and I'm a huge fan.

Artin admits he hasn't used popular mental wellness apps but acknowledges their value based on friends' experiences.

The breathing part is always the most profound for me.

He shares his personal experience with yoga and the impact of breathing exercises on his mental health.

Quick Fire Round: Personal Preferences and Investment Insights

  • Artin reveals his favorite book, "Fight Club," for its perspective on questioning the status quo.
  • He identifies a major red flag in investing: when the entrepreneur knows less about the sector than he does.
  • Artin shares his favorite newsletters, Ben Evans's mobile newsletter and StrictlyVC, for their focused content.
  • He discusses a unique app from the New York Times about 36 questions to fall in love, which he uses to deepen friendships.
  • Artin's most recent investment, PolicyGenius, was chosen due to the massive market and founders' expertise in relevant areas.

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.

Artin explains his investment decision-making process, highlighting the importance of the entrepreneur's expertise in their business sector.

It's a tie. I'm a huge fan of Ben Evans and his mobile.

He expresses his preference for specific newsletters that provide quality analysis and cater to his interests.

New York Times released this article and an app alongside it a while ago, which was 36 questions that lead to falling in love with somebody.

Artin shares his fascination with an app designed to foster deep personal connections through meaningful questions.

We did an investment out of New York called policy Genius.

He provides insight into his investment strategy, focusing on the potential of the market and the strengths of the founding team.

Endorsements and Recommendations

  • Harry Stebbings promotes the blog and sister show 'Angel Insights' for insights on angel investing.
  • He shares testimonials from Hiring Screen customers, emphasizing the platform's efficiency in the hiring process.

All the incredible resources mentioned in today's fantastic show with our team can be found on the blog at WW dot the twentyminutevc.com.

Harry directs listeners to the blog for resources mentioned in the show, demonstrating the value of supplementary content for the audience.

Another partner at a firm said that being able to send feedback to every applicant made her feel so much better about the entire hiring process.

Harry shares customer feedback on Hiring Screen, highlighting the positive impact of the service on the hiring experience.

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