James Bailey

Examiner
DISC Type : sc

Founder and Managing Partner at Bail Capital

United States

Overview

James Bailey is the Founder and Managing Partner of Bail Capital, a venture firm focused on the cannabis sector. A Harvard University graduate, he previously co-founded Velos Partners and held roles at Upfront Ventures and TA Associates, building a career in early-stage and growth investing.

He has a demonstrated interest in alternative health and wellness, shown through significant philanthropic support for psychedelic-assisted therapy research. Publicly, he is noted for his marriage to model and actress Devon Aoki, with whom he has children.

James was an early investor in prominent cannabis technology companies, including Eaze and PAX Labs.

Personality Overview

Tough To Convince

Process Oriented

Unexpressive

They are quite aware of their needs and limitations, so they are unlikely to over-promise.  Being observant comes to them naturally. They are heavily focused on quality and prefer doing things the right way, even if it takes time.

Topics They Care About

Cannabis Investing
As the founder of Bail Capital, he actively invests in cannabis technology and brands, including companies like Eaze, PAX Labs, and High Times.
Venture Capital
He has extensive experience as a venture capitalist, having co-founded Velos Partners and worked as an associate at Upfront Ventures and TA Associates.
Psychedelic Therapy
He donated $1 million to support research into MDMA-assisted psychotherapy for treating PTSD, showing a strong philanthropic interest in mental health solutions.

Media Appearances

James has no verified media appearances

Work History

1-2015 - 5-2025
Founder and Managing Partner at Bail Capital
1-2013 - 5-2025
Co Founder and Managing Director at Velos Partners
1-2010 - 12-2012
Associate at Upfront Ventures
Managing Director at Wilderness Point Ventures
7-2010 - 9-2010
Analyst at TA Associates

Education

2004 - 2009
Education details unavailable from Harvard University
Education details unavailable from Shady Hill

More Information

Social Presence :

Prographics :

Exp : 12 Location : United States Job Level : Mid-senior Designation : Founder and Managing Partner at Bail Capital
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Insights For Selling To James

During A Call Or A Meeting

DO's

  • First of all, focus on building their confidence by sharing examples, case studies etc.
  • Spend time addressing concerns around risk and change, they will have them even if they don't express them
  • Ask them which other stakeholders would be important for this purchase decision

DONT's

  • Don't be very accepting if that is your natural style, stay firm
  • Avoid getting into storytelling mode, especially when they ask specific questions
  • Don't rely on relationship building even if they act pleasantly

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with James is

  • Adoption by others is very important to them, followed by confidence in ROI.
  • Will you ever get a clear answer from James

  • They are unlikely to say no, it's better to stop yourself once you have exhausted all the options.

Insights For Deal Planning

    How fast (or slow) will James move?

  • They don't like to hasten, so their speed of decision-making may be slow.
  • Can James take some risk or not?

  • They have little willingness to take risks, and prefer making calculated decisions.

You And James

Personality Compatibility


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