Michael Dearing

Background

Michael Dearing is the founder of Harrison Metal, a seed-stage investment firm he started in 2008 ¹. He co-founded the firm with Erik Rannala, a fellow former eBay executive; Rannala departed in 2011 to start Mucker Capital in Los Angeles ². The firm is named after John Harrison, the 18th-century inventor of the marine chronometer ³.

Dearing earned an AB in Economics with a focus in economic history from Brown University and an MBA with Distinction from Harvard Business School ¹. Before entering venture capital, he spent six and a half years at eBay, rising from category manager of furniture and appliances to Senior Vice President and General Merchandise Manager of eBay North America, where he was responsible for more than $1.7 billion in annual revenues and nearly $20 billion in gross merchandise sales ¹. He led the development of features including Buy It Now, eBay Stores, ProStores, and Want It Now ¹.

Prior to eBay, Dearing held roles at The Walt Disney Company (corporate strategy), Industrial Shoe Warehouse (COO then CEO), Filene’s Basement (operations), and Bain & Company (Associate Consultant) ¹.

From 2006 through 2014, Dearing served as a Consulting Associate Professor at Stanford University’s School of Engineering, teaching classes in Mechanical Engineering, Management Science & Engineering, and the d.school ¹. His courses included Launchpad and Creating Infectious Action ⁴. Kara Swisher dubbed him “the hottest angel investor you’ve never heard of” in 2010 ³.

As General Partner, Dearing manages Harrison Metal’s six funds, whose limited partners include university endowments, charitable trusts, and pensions ¹. The firm’s fifth fund closed at $68 million in March 2018 ⁵. Total assets under management are estimated at over $200 million across all six funds ⁶.

Stated Thesis

Harrison Metal describes its investment philosophy through the lens of business and economic history, valuing “mutually beneficial trade” as a core principle ¹. Dearing has stated that his thesis centers on “turning experts inside larger companies into founders of startups,” believing this creates winning investment opportunities analogous to comparative advantage in global trade ⁷.

In a StrictlyVC interview, Dearing identified management as the critical bottleneck for startups: “The scarcest input in our system right now has been in short supply for 200-plus years of industrial capitalism — exceptional general management” ⁷. He has argued that “bad management and leadership kills more startups than bad products” ⁸.

Dearing’s framework for evaluating founders centers on five cognitive traits he calls “the cognitive distortions of founders” ⁹. The most prominent is “personal exceptionalism” — founders who believe “their outcomes are going to be outside the bounds of normal” for their peer group ⁸. He also looks for high iteration velocity, noting that “their impatience and their ability to iterate their product is hugely important” ⁸.

On company structure, Dearing has advocated for what he calls “benevolent dictatorship,” stating that “when CEOs can master benevolent dictatorship, it is a beautiful thing” and that “we pay people for their judgment. We don’t pay people to run AB tests” ⁸.

On the Heavybit blog, Dearing has described pricing as a judgment problem rather than a math problem, using behavioral economics to enhance standard supply-and-demand models ¹⁰.

Inferred Thesis

Based on 30 verified investments below, Harrison Metal’s actual portfolio reveals:

Sector distribution: Enterprise software and developer tools represent the largest share, with 12 of 30 investments (40%) in enterprise/developer tools (PagerDuty, Signal Sciences, CircleCI, Heroku, MoPub, StackMob, Recurly, Mixmax, ClearBrain, Quilter, CoreStory, Toolchain Labs). Consumer-facing companies account for 10 of 30 (33%), including MasterClass, Birchbox, Harry’s, Polyvore, ModCloth, Good Eggs, 99designs, BloomSpot, MocoSpace, and Lumos Labs. The remaining 8 of 30 (27%) span categories including health tech (Grand Rounds/Included Health, Vital Interaction), edtech (Guild, AltSchool), adtech (AdMob), social search (Aardvark), ecommerce infrastructure (CafePress, DocVerse).

Stage distribution: Harrison Metal has made 59 of its total investments at the seed stage, with an average seed round size of $2.39 million ¹¹. The firm’s portfolio composition is approximately 55% seed, 26% Series A, 6% Series B, and 2% Series C ⁶. This confirms a strong seed-stage orientation with selective follow-on investing.

Check size: Dearing’s typical investment range is $200K to $2M, with a target of $500K for initial checks ¹²¹³. The seed sweet spot is $1M to $2.5M for initial investments ¹¹.

Geographic concentration: The portfolio is overwhelmingly US-based, with heavy concentration in San Francisco and the Bay Area. Consumer companies like Harry’s (New York) and Birchbox (New York) are notable exceptions ¹¹.

Founder profile patterns: Dearing has a demonstrated preference for founders with prior experience at large technology companies. MoPub’s team was entirely ex-AdMob/ex-Google ¹⁴. MasterClass founder David Rogier was a former Harrison Metal employee and Stanford MBA student under Dearing ¹⁵. Aardvark co-founder Max Ventilla went on to found AltSchool, which Dearing also backed ³.

Co-investor patterns: Accel Partners appears as a frequent co-investor (MoPub, Birchbox, 99designs). Baseline Ventures co-invested in PagerDuty and Heroku. The firm operates as a solo-GP fund and typically does not lead rounds ¹³, though it has led some seed rounds.

Notable gap: Despite describing itself as sector-agnostic, the firm has minimal exposure to fintech and biotech, which are not represented in the verified portfolio.

Deployment pace: Investment pace has slowed significantly in recent years, from approximately 11 new investments per year in 2017-2018 to 1 in 2024 and 1 in 2025, suggesting the firm may be between funds or winding down new investments ⁶.

Portfolio

This table represents approximately 30 of 107 known investments (~28%). The analysis is based on publicly verifiable data; many early angel investments lack detailed public records ¹¹.

In Their Own Words

“The scarcest input in our system right now has been in short supply for 200-plus years of industrial capitalism — exceptional general management.” — Michael Dearing, StrictlyVC interview, December 2014 ⁷

“Bad management and leadership kills more startups than bad products.” — Michael Dearing, 20VC podcast ⁸

“Convertible debt. Yuck. Treat yourself to real shareholders who rise and sink with you from day one.” — Michael Dearing, Twitter, September 2015 ²⁴

“More convinced than ever that gross margin is nature’s way of telling you whether you should keep going or stop.” — Michael Dearing, Twitter, April 2016 ²⁵

“Pricing is the way that we manage our risk, it’s the primary tool I have.” — Michael Dearing, 20VC podcast ⁸

“Where you get into trouble is in the high-flying private deals where the leadership takes out a ton of money in secondary sales.” — Michael Dearing, StrictlyVC interview, December 2014 ⁷

“The very best early-stage investor in the business is Steve Anderson. Tells the truth. Focuses on making the pie big first.” — Michael Dearing, StrictlyVC interview, December 2014 ⁷

“Ten years ago this month, I started this business. I was excited-nervous as could be.” — Michael Dearing, on Harrison Metal’s tenth anniversary, March 2018 ⁵

“We pay people for their judgment. We don’t pay people to run AB tests.” — Michael Dearing, 20VC podcast ⁸

What Founders Say

“Michael was among the very first angel investors to get behind Aardvark and stayed critically involved until the end, providing whatever the Company needed. Dearing is an 11 out of 10.” — Max Ventilla, co-founder of Aardvark, AllThingsD, February 2010 ³

“MD is a great strategist and provided us with very thoughtful advice during some of the formative days of the company.” — Omar Hamoui, founder and CEO of AdMob, AllThingsD, February 2010 ³

“Michael Dearing has the very rare skill of being able to quickly spot and render the core elements of strategy surrounding a project — the things that matter and those that don’t.” — Bijan Marashi, co-founder and CEO of Xoopit, AllThingsD, February 2010 ³

Connections

• Board member, Guild — current board seat ²³
• Board member, Mixmax — current board seat ²³
• Board member, Signal Sciences — joined board in 2014; Signal Sciences acquired by Fastly for $775M in 2020 ²⁰²³
• Board member, Toolchain Labs — former board seat ²³
• Board member, Included Health (formerly Grand Rounds) — former board seat ²³
• Former SVP, eBay (2000-2006) — worked alongside Erik Rannala, who co-founded Harrison Metal ¹²
• Consulting Associate Professor, Stanford University (2006-2014) — taught David Rogier (MasterClass founder) in MBA program ¹⁵
• Co-investor with Accel Partners — MoPub, Birchbox, 99designs ¹⁴¹⁸¹⁹
• Co-investor with Baseline Ventures — PagerDuty, Heroku ¹⁶¹⁷
• Heavybit community member — presented on pricing and executive communication ¹⁰
• Grace Science Foundation board member ²⁶

Sources