For this episode, I interviewed Eugene Malobrodsky, partner at One Way Ventures and former founder of AnchorFree, the company behind HotSpot Shield, one of the first consumer VPN products to scale globally.

Before becoming a VC, Eugene spent 15 years building and scaling a startup through the 2008 financial crisis, painful layoffs, difficult fundraising environments, and the long grind from idea to acquisition.

Today, he backs immigrant founders building applied AI, deep tech, fintech, healthcare, and enterprise startups at the pre-seed and seed stage.

Topics include:

Why many founders become founders for the wrong reasons
What venture capitalists really mean when they talk about “100x outcomes”
How to think about fundraising runway and dilution
Why technical founders often struggle with storytelling
What makes a startup venture-backable versus a profitable lifestyle business
The most common mistakes early technical teams make
How investors evaluate first-time founders with no track record
Why customer discovery matters more than building features too early
Why the best founders are often “angry at the problem” they’re trying to solve

He also spoke about what immigrant entrepreneurs misunderstand about networking in Silicon Valley, and the growing uncertainty around H-1B visas and startup immigration policy.

RUNTIME 56:28

EPISODE BREAKDOWN

(2:13) "I'm just not great at following directions and working for somebody else."

(5:44) How Working in VC Changed His Thinking

(7:42) What Founders Misunderstand About VC Funds

(20:53) A Practical Framework for Seed-stage Fundraising

(25:50) What Makes Him Take the Meeting

(31:19) Where One Way Ventures is Betting in Deep Tech

(35:11) The Most Common Mistakes Technical Teams Make

(38:23) Why Founders Need a 90-second Story

(43:16) Growing Uncertainty for Immigrant Tech Workers and Founders

(51:33) Practical Networking Advice for First-time Founders

(54:38) The One Question H1-B Candidates Should Ask the CEO During an Interview

LINKS

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Thanks for listening!

– Walter