Todd Masonis
Angel Investor; Co-Founder & CEO, Dandelion Chocolate at Long Journey Ventures
Reviewed Updated Aug 5, 2026This profile is AI-generated. If you spot an error, please help us fix it by sharing a URL to the correct information.
Background
Todd Masonis is an angel investor and the co-founder and CEO of Dandelion Chocolate, a bean-to-bar chocolate maker based in San Francisco’s Mission District 12. He is best known in tech circles as one of the co-founders of Plaxo, the address-book synchronization service he co-founded with Stanford classmate Cameron Ring and Sean Parker in 2001-2002 34. Masonis and Ring were the “two Stanford University engineering students” who built and ran the company after Parker’s 2004 departure 35. Plaxo launched in public beta on November 12, 2002 3, grew to roughly 20 million users, and was acquired by Comcast in a deal announced May 14, 2008 and closed July 1, 2008 for a reported $150-170 million 56.
After selling Plaxo, Masonis took a sabbatical and, with Ring, began experimenting with chocolate-making — first in a friend’s garage, then at farmer’s markets — before opening Dandelion Chocolate as a small-batch bean-to-bar factory in 2010 27. His wife and Stanford classmate Elaine Wherry (also a Plaxo co-founder) is a co-founder of Dandelion Chocolate and is closely associated with the venture-capital firm Long Journey Ventures (formerly Edelweiss), where she serves as an Advisor 89.
As an angel investor, Masonis has been listed as a syndicate member of the AngelList “Edelweiss” syndicate that is affiliated with Long Journey Ventures 10. Long Journey Ventures itself was originally founded in 2015 as Edelweiss by Lee Jacobs with operator partners Brian Balfour, Elaine Wherry, and Jonathan Bruck; the firm rebranded as Long Journey Ventures in 2020 and Masonis is not listed on its current team page 911. His angel investing is primarily reported on his own name, and public records show a modest, individually-sourced portfolio (see Portfolio below).
Stated Thesis
Masonis has not published a formal investing thesis. His publicly available statements focus on operating philosophy rather than investment criteria. In interviews about Dandelion Chocolate, he has emphasized product quality over speed and a bias toward starting with the smallest possible version of a product:
“The problem is you don’t have a product. For us, it was: Could we make a bar of chocolate? We made a bar of chocolate. Could we make two bars?” 7
“Do not compromise quality for speed efficiency” 12
Because there is no published investment thesis, the sections below rely on inferred behavior and general operating principles Masonis has articulated.
Inferred Thesis
Sample size is small. Independent public sources report only a handful of confirmed personal angel investments by Masonis — PitchBook and Crunchbase-derived aggregators variously report 2-5 investments, with his most recent verified check being a 2022 seed round in Valence 1314. Because the sample is so small, percentages would be misleading. The following qualitative patterns are visible in the confirmed data:
- Operator-angel style, not full-time investor. Masonis’s primary role has been operating (Plaxo, then Dandelion Chocolate); his angel checks are made as an ex-founder writing personal checks, often alongside other operator-angels from the Plaxo network. MediaSpike’s 2013 Series A, for example, included “seven people from Plaxo” as angel investors, of which Masonis was one 15.
- Consumer, food, and marketplace bias. Confirmed personal investments cluster around consumer-facing companies — Foodzie (artisan food marketplace, exited to Joyus in 2012), BrightCrowd (consumer collaboration), and Valence (professional network for Black professionals) 1314. This is consistent with his own operating focus on consumer product.
- Bay Area geographic focus. All confirmed personal investments are US-based, primarily in the San Francisco Bay Area, which matches his network and physical location 13.
- Syndicate participation via Edelweiss/Long Journey. Beyond personal checks, Masonis is a listed team member of the AngelList “Edelweiss” syndicate affiliated with Long Journey Ventures, which sources deals to operator-LPs 10. Participation in that syndicate is a distinct activity from Long Journey’s core fund — Masonis is not listed as a partner, venture partner, or advisor on Long Journey’s current team page 11.
Note on aggregator data. Multiple third-party aggregators (Wellfound, Bloomberg, Tracxn) describe Masonis as an “Edelweiss” investor and attribute investments in Fitbit, Honor, HipChat, Blue Bottle Coffee, HoneyBook, Loom, and others to “Edelweiss.” These may or may not correspond to personal Masonis checks — they most likely reflect Edelweiss/Long Journey fund investments and syndicate deals rather than his personal cap-table participation. Because we could not verify Masonis’s personal participation in those specific rounds from a primary source, they are not included in the Portfolio table below.
Portfolio
Only investments with a verifiable public source of Masonis’s personal participation are included. This is a deliberately conservative table.
| Company | Year | Stage | Source |
|---|---|---|---|
| Foodzie | ~2008 (founding-year proxy) | Angel/Seed | Listed as exit on PitchBook/Crunchbase-derived aggregators; company acquired by Joyus in June 2012 1316 |
| MediaSpike | 2013 | Series A | Named participant as one of “seven people from Plaxo” in $5.2M Series A led by CMEA Capital 15 |
| BrightCrowd | ~2016 | Seed | Listed as Masonis seed investment on Crunchbase-derived aggregators 13 |
| Valence | 2022-05-03 | Seed | Listed as Masonis’s most recent verified investment on Foundersuite 14 |
This table represents fewer investments than some aggregators claim (which range from 2 to “an army of investors” participation). We prioritized primary-source verifiable rounds over aggregator counts. If Masonis’s team has a more complete list, we would incorporate it.
In Their Own Words
On starting small and shipping the smallest possible product:
“The problem is you don’t have a product. For us, it was: Could we make a bar of chocolate? We made a bar of chocolate. Could we make two bars?” 7
On downside risk as an entrepreneur:
“The worst case scenario is that you go back to the life you’re living right now; no use in worrying.” 12
“If you fail, you can just go back to working like you did before.” 12
On product quality:
“Afraid of having chocolate that just tastes like everyone else’s chocolate.” 12
On Plaxo’s founding:
“I had started a company called Plaxo with my friend Cam and Sean Parker in 2001, the year we graduated.” 7
What Founders Say
No independently sourced founder testimonials about working with Todd Masonis as an angel investor were found in this research pass.
Sources
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Dandelion Chocolate, “Making Chocolate: From Bean to Bar to S’more” (product page listing Todd Masonis as co-founder), accessed August 2026. https://www.dandelionchocolate.com/products/making-chocolate-from-bean-to-bar-to-smore↩
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“Todd Masonis at General Assembly” (instructor bio identifying him as CEO and Co-founder of Dandelion Chocolate), accessed August 2026. https://generalassemb.ly/instructors/todd-masonis/8123↩↩
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Wikipedia, “Plaxo” (co-founders Sean Parker, Todd Masonis, Cameron Ring; November 12, 2002 launch), accessed August 2026. https://en.wikipedia.org/wiki/Plaxo↩↩↩
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Grokipedia, “Plaxo” (Parker + two Stanford engineering students Masonis and Ring), accessed August 2026. https://grokipedia.com/page/Plaxo↩
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“Sean Parker’s other notorious startup, Plaxo, is finally dead — here’s how it influenced Facebook,” Yahoo Finance, accessed August 2026. https://finance.yahoo.com/news/sean-parker-apos-other-notorious-191419877.html↩↩
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“Comcast buys social networking firm Plaxo for $175m,” Campaign, accessed August 2026. https://www.campaignlive.co.uk/article/comcast-buys-social-networking-firm-plaxo-175m/809404↩
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“How They Made It: Todd and Elaine of Dandelion Chocolate on work and marriage,” Ava Bear, accessed August 2026. https://www.avabear.xyz/p/how-they-made-it-todd-and-elaine↩↩↩↩
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Long Journey Ventures, “Team” page (Elaine Wherry listed as Advisor; Masonis not listed), accessed August 2026. https://www.longjourney.vc/team↩
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Long Journey Ventures, “Long Journey: The Beginning” (founding history — Lee Jacobs raised Edelweiss in 2015 with Balfour, Wherry, Bruck; renamed 2020), accessed August 2026. https://www.longjourney.vc/news/lee-jacobs-welcome-long-journey-ventures↩↩
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AngelList, “Invest with Long Journey Ventures’ Syndicate” (Edelweiss syndicate page listing Todd Masonis as a team member), accessed August 2026. https://venture.angellist.com/edelweiss/syndicate↩↩
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Tracxn, “Long Journey Ventures — Investor Profile” (current team, formerly known as Edelweiss), accessed August 2026. https://tracxn.com/d/venture-capital/long-journey-ventures/__3ci8jkwGn7fhtAohltp8tGb-bjViZ_-ltxBxhdC3oWs↩↩
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“Todd Masonis – Co-Founder, Dandelion Chocolate,” Habits of Entrepreneurs, accessed August 2026. https://habitsofentrepreneurs.com/dandelionchocolate/↩↩↩↩
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Crunchbase, “J. Todd Masonis” person profile (angel investments, exits including Foodzie), accessed August 2026. https://www.crunchbase.com/person/j-todd-masonis↩↩↩↩↩
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Foundersuite, “Todd Masonis | Investor profile” (latest investment: Valence, May 3, 2022), accessed August 2026. https://www.foundersuite.com/investors/todd-masonis↩↩↩
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“MediaSpike raises $5.2M from army of investors for in-game ads,” GamesBeat, November 4, 2013 (lists “seven people from Plaxo” as angel investors in the Series A), accessed August 2026. https://gamesbeat.com/mediaspike-raises-5-2m-for-in-game-product-placement-ads/↩↩
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“Food Subscription Service Foodzie Gets Gobbled Up By Video Shopping Network Joyus,” TechCrunch, June 5, 2012, accessed August 2026. https://techcrunch.com/2012/06/05/foodzie/↩