Alessandro Chesser in

Alessandro Chesser

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CEO at Dynasty
📍 Orinda, California, United States

Alessandro Chesser is the CEO of Dynasty, helping startup founders with QSBS trusts. A San José State University graduate, he was formerly the first sales hire at Carta, where he was instrumental in scaling revenue from zero to over $300 million and launching eight new business lines.

Colleagues consistently describe him as having significant grit, being a bright mind, and employing creative methods to solve problems for clients. He maintains a strong connection to his alma mater, San José State University, which he lists as a primary interest.

He has a keen interest in business strategy, believing that the only true moat for a company is a regulatory license that competitors lack.

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Experience
14 Years
Current Role
CEO
Job Level
Leadership
Location
Orinda, California, United States
Personality Overview

How Alessandro shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Alessandro cares about

QSBS Trusts
His current company, Dynasty, is entirely focused on helping startup founders utilize Qualified Small Business Stock (QSBS) and trusts to maximize their financial outcomes.
Founder Wealth
He is passionate about solving wealth management problems for startup founders and has built his current business around this specific niche.
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Career

Work history

2-2022
CEO
Dynasty
10-2014 - 5-2022
VP of Sales
Carta
4-2013 - 9-2014
Account Executive
Quantcast
5-2012 - 4-2013
CapMx Account Manager
Solium
3-2011 - 5-2012
CapMx Account Representative (Acquired by Solium May 2012)
SVB Financial Group
In the press

Media appearances

The Get Dynasty Origin Story - The Higher Standard. Featured in Apple Podcasts
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Success Interview: Alessandro - CEO of GetDynasty. Featured in YouTube
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Education
2003 - 2008
Bachelors of Science
San José State University
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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