Startup.
Everything I've written about startup. Start at the top; the list compounds.
The Operating Cadence I Run for SMB Clients (and Why Weekly Beats Daily)
When I started taking on fractional CTO and operational advisory engagements, I defaulted to the cadence I knew from agency life: daily standups, weekly status reports, and monthly strategy reviews. Three months into my first few engagements, I noticed somethi
Build Internal Tools Before Customer-Facing Ones: The Order That Saved Me Six Months
When I was setting up my third company, a B2B SaaS serving SMB clients in the real estate sector, I made a decision that felt wrong at the time and turned out to be the most operationally correct thing I did in the first year. Instead of building the customer-
When to Stop Bootstrapping and Raise: A Decision Tree With Real Numbers
Most founders I talk to treat the bootstrapping-versus-raising decision as a values question. Do you want to maintain control? Do you believe in the VC model? Are you building a lifestyle business or a venture-scale company? These are real questions worth answ
Killing a Product Line Without Killing the Company
In 2022, I helped a SaaS company shut down a product line that represented 35% of their revenue. It was the right decision. It was also terrifying, slow, and handled worse than it should have been. By the time we finished the wind-down, we had lost two custome
Hiring a Fractional CTO: The Scope, Cadence, and Red Flags
I have been the fractional CTO for over 20 SMB and SaaS companies at various stages. I have also watched founders hire the wrong person for this role repeatedly, in ways that are entirely predictable and largely preventable. This note covers what the role actu
Hiring Your First Engineer: The Trial Project That Actually Predicts Performance
The standard software engineering interview was designed to filter hundreds of candidates for a large company with predictable, well-scoped work. It was not designed for a three-person startup with an ambiguous problem and a codebase that changes direction eve
The First 90 Days as a Solo Technical Founder: A Week-by-Week Playbook
The first 90 days as a solo technical founder are the most leveraged and most wasted period in any startup's life. You have no customers to disappoint, no investors to report to, and no team to coordinate. You have total freedom and total ambiguity. Almost eve
Why 'Talk to Customers' Is Bad Advice, and the Five-Question Interview That Replaces It
"Talk to your customers" is the most repeated piece of startup advice and one of the least actionable. I have told founders this myself, in exactly those words, and then watched them come back from ten customer conversations having learned almost nothing usefu
Cofounder Disputes: The Operating Agreement Clauses Most Templates Forget
Most cofounder disputes are not about personality. They are about ambiguity. Two people build a company together, write an LLC operating agreement (or do not write one), and then discover at a critical moment that they have different assumptions about who owns
The Pre-Seed Stack: What to Build Yourself, What to Buy, What to Skip Entirely
The first engineering decision at most startups is made wrong. Not because the founders are inexperienced, but because the framing is off. "What should we build?" is the wrong question. The right question is: what is the smallest set of things we must build to
Equity Splits That Survive Five Years: A Framework Beyond Let's Just Go 50/50
The 50/50 split is not a decision. It is a postponed decision. Two founders who cannot agree on relative contribution, relative risk, and relative future commitment choose 50/50 because it avoids a conversation they are not ready to have. The problem is that t
Runway Math for Non-Finance Founders: The Spreadsheet I Wish I'd Had at Seed
Most non-finance founders get their first real lesson in runway math from an investor who says "your burn looks high." By that point, you are usually three months from the problem, not three months from the solution. I have acted as the de facto CFO (through t