Daniel Vassallo

Observer
DISC Type : ci

Working for myself at Small Bets

Greater Seattle Area, United States

Overview

Daniel Vassallo is an entrepreneur and former Amazon Web Services software engineer who founded the online community "Small Bets". He leveraged his background, including a Bachelor of Science from the University of London, to build and successfully sell his business to Gumroad, championing a philosophy of sustainable, independent entrepreneurship.

Based in the Pacific Northwest, Daniel has built a lifestyle centered on financial freedom and self-employment after leaving the corporate world. He recently turned 40 and often shares insights from his personal and professional journey with his online audience, showing an appreciation for his regional surroundings.

He successfully sold his bootstrapped business, Small Bets, for $3. 6 million.

Personality Overview

Curious

Example Seeker

Value Driven

They ask a lot of questions and rely heavily on information and collaterals.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They are generally strong communicators and are not easy to convince.

Topics They Care About

Small Bets Philosophy
He champions building small, sustainable, and profitable internet businesses over pursuing high-risk, venture-backed startups.
Online Communities
He built, grew, and sold the "Small Bets" community, which generated $400K in annual revenue, demonstrating deep expertise in community management.
Financial Independence
His career centers on leaving traditional employment at companies like Amazon to create self-directed, independent income streams.

Media Appearances

Taking small bets with Daniel Vassallo [#34]. Featured in Apple Podcasts

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22/ Daniel Vassallo: Building credibility through small bets. Featured in Spotify

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Building a Portfolio of Small Bets | Daniel Vassallo. Featured in Spotify

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Work History

5-2019
Working for myself at Small Bets
7-2012 - 2-2019
Software Development Engineer at Amazon Web Services
11-2010 - 7-2012
Software Development Engineer at Amazon Web Services
10-2008 - 4-2010
Software Developer at Cyber Pass Ltd

Education

Bachelor of Science from University of London

More Information

Social Presence :

Prographics :

Exp : 16 Location : Greater Seattle Area, United States Job Level : N/A Designation : Working for myself at Small Bets
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Insights For Selling To Daniel

During A Call Or A Meeting

DO's

  • Invite them for a social do but don’t rely solely on the relationship
  • Help them realize that there is no personal risk in making this decision
  • Share testimonials from known people and give multiple examples of product value

DONT's

  • Don’t be too objective but make sure to pad your storytelling with data points
  • Don’t brush off any concerns, take all questions seriously
  • Don’t rely excessively on your relationship with them to win the deal

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Daniel is

  • Proven value, strong testimonials are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Daniel

  • They are practical yet friendly, don’t expect a clear no very often.

Insights For Deal Planning

    How fast (or slow) will Daniel move?

  • They like to analyze well and can take their time to reach any decisions.
  • Can Daniel take some risk or not?

  • They weigh all decisions systematically and are unlikely to take many risks.

You And Daniel

Personality Compatibility


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