Investors, Innovators, Influencers – Alex Iskold


After planting roots in engineering, Alex Iskold moved into the startup landscape, where he founded two companies before becoming the Managing Director at Techstars. Now a Managing Partner at 2048 Ventures, Alex has invested in over 100 companies; he believes that when you mix vision with empathy and discipline, you find magic.

Tell us about the professional journey that took you where you are today. What major lessons did you learn along the way?

My family immigrated to USA in 1991 and since then I’ve been on an incredible journey – first as an engineer then as a 2x startup founder and most recently as a Managing Director at Techstars and now 2048 ventures. In the last 5 years I’ve invested in over 100 companies and I learned my strength as an investor. My super powers are that I have empathy for the founders I work with and that I can see the future as an engineer and a tech nerd. When you mix tech vision with empathy and discipline thats where the real magic happens.

What motivates you?

Our mission is to back first time founders and founders which have first time founder mindset who are working on companies differentiated through technology. I love working with founders, being there for them when things aren’t going well and staying out of their way and cheering them on when they are crushing it.

What do you look for in a potential investment?

Strong founder market fit, early traction, strong vision and resilience.

How do you find and curate your deal flow? What are the most effective ways for a founder to connect with you?

Our deal flow comes from our massive network of founders, execs, LPs, friends of the firm, angels and VCs.

What are the major trends you are seeing in your investment space?

Everything is becoming tech. Software is eating the world. Data is eating the world. Every single company is becoming a technology company.

What are a few of the investments that you are the most proud of, regardless of the company’s success?

I am proud of all but maybe 2-3 investments out of 100 companies I backed. When I am not proud is when I found that founders behaved in a way that I don’t believe to be worthy, but otherwise I am proud of the founders. The qualities of the founders I backed that I am most proud of is their drive, incredible hard work, and giving their all to the businesses they are building. Some of the fastest growing companies I backed include DataCamp – online school for data science, Mantl – banking core infrastructure, Pilot – ultrafast fiber optic internet provider, BentoBox – platform for hospitality industry, GreatHorn – spearfishing prevention platform, GlossGenius – intelligent assistant for beauty professionals, Gorgias – AI-based help desk for e-commerce, Hawthorne – personalized men care products, and many others. I am excited about portfolio companies like De-Ice – new way to de-ice airplanes, PathSpot – device for detecting food-borne illnesses, Rootine – solid form personalized vitamins based on your DNA and blood sample, that are creating technologies of the future.

What do you wish founders knew about before meeting you and other investors? What about female founders specifically?

I’ve written a lot on this topic on my blog called Startup Hacks, which has over 60 posts, a lot of them about how to prepare to raise capital. The number one thing is prepare – don’t fundraise randomly before you are ready. Target the right investors and know why you would be a fit. For me personally I love it when founders send me a video pitch, and I love founders who have massive visions on what the world is going to look like in coming decades.