Ben is raw and honest about the agonizing reality of running a startup. That's why I love it.
View on Goodreads ↗01 About
I build the operating backbone early-stage startups need when they outgrow how they run. I rebuild GTM, install the cadence, and bring structure to execution — across operations, strategy, fundraising, hiring, finance, and automation, wherever the leverage actually is.
- Scaled a deep tech startup from 18 to 55 people as Chief of Staff and then COO. Grew revenue 120% YoY on average and reached profitability. Sold to a strategic buyer.
- Ran a $30M investment pipeline and structured $22M+ in debt deals at a private equity firm; interim operator at portfolio companies.
- Co-founded an investment and advisory firm and grew it from 3 people to 25, managing a $65M+ portfolio of distressed assets. Sold to a banking group.
If you're a founder who has become the bottleneck, that's the work I want next. I'm looking for a Head of Operations or Chief of Staff role at a startup hitting that inflection point — on-site (I'll relocate for the right one) or remote.
02 Career
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2024 — 2026Head of Operations / Chief of StaffBoston, MA
GTM, sales ops, and the layer underneath that usually breaks. Cleaned up targeting, pricing, and the manual busywork around outbound — improving close rates to 65%+ and lifting revenue 20%+. Launched a daily newsletter and ad platform that became a new revenue line.
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2024 — 2026Strategy & Operations AdvisorSan Francisco, CA
Payments startup building a checkout layer that lets shoppers combine multiple cards, wallets, and account balances in a single purchase.
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2019 — 2024WebgearsRedwood City, CA
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2023 — 2024Strategic Advisor
Post-acquisition transition and continuity.
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2021 — 2023Chief Operating Officer
Ran the business side of a deep tech startup as it scaled from 18 people to 55 and was acquired. GTM across multiple verticals, partnerships with Google and Autodesk, P&L, hiring — everything that wasn't the 3D engine itself. Revenue grew 120% YoY on average.
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2019 — 2021Chief of Staff
Strategy, finance, hiring, and cross-functional execution — translating founder priorities into operating plans with real follow-through. Raised $4.6M in pre-seed and seed.
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2015 — 2018Managing Director / Equity PartnerSkySail Investment ManagementMoscow
A mix of investing and operating. Managed a $30M pipeline, put together $22M+ in debt deals, and stepped in as interim operator when portfolio companies needed one.
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2008 — 2015Managing Director / Co-FounderClarus CapitalMoscow
Built an investment and advisory firm from three founders to twenty-five people, overseeing $65M+ in distressed assets. Ran day-to-day operations and client work across restructuring, interim management, and asset sales. Sold to a banking group.
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2004 — 2008Sr. Business Analyst / Project ManagerArbella Insurance GroupQuincy, MA
Underwriting systems, fraud detection, and product expansion into new markets.
03 Open Source
Open-source tools for the work itself. Mostly Claude Code skills and operating tooling.
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faultline Shipped
Pressure-tests early-stage operations work with sharp, context-grounded questions. The kind a good board member would ask before you noticed the gap yourself.
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skill-safety-check Shipped
Static safety triage for agent skills. Point it at a repo or paste a skill and get a SAFE / REVIEW / DO NOT INSTALL verdict before you run it.
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llm-knowledgebase Shipped
A safe, local LLM knowledge base with immutable sources and an agent-maintained Markdown wiki. The sources can't drift; the wiki on top of them can.
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DeAI Shipped
A self-review skill that catches AI tells, voice mismatches, and weak substance in written work — before a human has to.
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My_Claude.MD Shipped
An opinionated CLAUDE.md baseline for planning, debugging, security, and verification in Claude Code.
04 Side Projects
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Pack or Stay Shipped
For anyone weighing a move between cities. Pick two metros, enter a salary, and it shows what each actually leaves you after taxes, housing and everyday costs — then answers in a word: pack, stay, or too close to call. Built on public data only — Census, BLS, IRS, the Tax Foundation — across 438 metro areas.
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Hi, Sweetie — Letters Shipped
Letters from a dad to his daughters, published as they're written.
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Political Compass In progress
An interactive atlas of political movements and parties — Democrats, Republicans, Libertarians, Anarchists and the rest — mapped so you can see how they actually relate to each other.
05 Bookshelf
Some of what's on the shelf. Arrows to browse, Why for the reason.
THE book for Chiefs of Staff - the origin and lessons on crisis management and leadership. Explains the reasons why Chiefs of Staff exist in the first place.
View on Goodreads ↗What an engaging view of American exceptionalism told through the history of innovation, economic shifts and development of commerce as we know it.
View on Goodreads ↗Provides lenses through which to view risk and accountability. A great tutorial on how to judge people (including myself) by what they risk, not what they say.
View on Goodreads ↗We aren't building monopolies, but first principles and critical thinking, challenging conventional wisdom is a virtue to learn and practice.
View on Goodreads ↗Makes you think just how fragile our civilization is and how dependent it is on the current tech stack.
View on Goodreads ↗Writing is thinking. Cutting academic fluff and bad habits from writing makes it clearer, adding rhythm and trust to one's thoughts. Worth a refresh.
View on Goodreads ↗Parallelism to reality aside, it's worth a re-read every time. Smartly written.
View on Goodreads ↗Fantastic guide on how not to die at sea, which is always worth the read time before ocean crossing.
View on Goodreads ↗Worth knowing where we all came from and how we use shared myths, like money and laws, to live together.
View on Goodreads ↗