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March 18, 2021

#283: Alex Iskold, Co-Founder and Managing Partner of 2048 Ventures, an Early Stage VC Firm Backing the Next Generation of Amazing Tech and Data Companies, on Founder Failure, His 5 Years at Techstars, The Future of Pre-Seed Investing, and

#283: Alex Iskold, Co-Founder and Managing Partner of 2048 Ventures, an Early Stage VC Firm Backing the Next Generation of Amazing Tech and Data Companies, on Founder Failure, His 5 Years at Techstars, The Future of Pre-Seed Investing, and

Alex Iskold is a co-founder and Managing Partner at , an early stage venture capital firm investing in exceptional first-time entrepreneurs who are building businesses differentiated through technology. Based in NYC, 2048 invests in founders from New...


Alex Iskold is a co-founder and Managing Partner at 2048 Ventures, an early stage venture capital firm investing in exceptional first-time entrepreneurs who are building businesses differentiated through technology. Based in NYC, 2048 invests in founders from New York, Boston and Emerging Tech Cities. Alex is a 4x founder, a software engineer, and an investor in over 110 startups. He writes one of the top startup blogs called Startup Hacks. Alex is also a co-founder of the 1kproject - a volunteer effort focused on pandemic relief. Prior to founding 2048 ventures, Alex spent 5 years at Techstars as the Managing Director of its NYC program. Alex was also the founder and CEO of Info Lab (acquired by IBM), founder and CEO of GetGlue (backed by USV, RRE, Time Warner), and a Chief Architect of distributed computing startup DataSynapse (acquired by TIBCO). Alex currently serves as a Coach and a VC in Residence at the Arthur Rock Center for Entrepreneurship at the Harvard Business School. Alex previously taught an award-winning undergraduate computer science class at NYU. He holds a B.S. in Math with Honors from Lehigh University and M.S. in Computer Science from NYU.

About Our Partner

This episode is brought to you Varia Search. Varia Search is a boutique legal recruiting firm that uses a bespoke approach to fill legal department roles from general counsel to paralegal. They have a particular focus on startups and growing tech companies.

They are a boutique firm which allows them to provide individualized, in-depth attention to both their clients and to their searches.

They focus solely on placing in-house candidates which allows them to give their clients a bespoke experience in filling their legal needs.

Their matchmaking approach ensures that clients are paired with candidates who not only have great credentials but who are also a good cultural fit for a growing company.

Learn more at variasearch.com.

Some of the Topics Covered by Alex Iskold in this Episode

  • How Alex "accidentally" got into VC
  • Being a 4-time founder and the challenges that he faced
  • Startup failure and knowing what's next
  • How his background in computer science and software engineering and his experience as a founder impacted his role at Techstars and as a VC
  • Why Alex decided to start 2048 Ventures and how he went about structuring the firm
  • The process of raising a $27M fund in 3 months
  • How they prepared to raise the fund and networked for LPs
  • How they think about ownership strategy and the institutional-caliber process they've developed
  • The challenges of pre-seed deal flow and sourcing and being geographically agnostic
  • What Alex has learned from building and running his own fund
  • How 2048 screens early stage companies
  • Evaluating founder-market fit
  • How Alex sees early stage investing (and the world) changing
  • How Alex curates the content he consumes
  • How he approaches industry deep-dives
  • What happens after the investment
  • Why Alex has his blog Startup Hacks and the culture of writing things down
  • How Alex manages his time and the myth of more hours

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