Six months into a round, I'm still sending the same follow up email about a condition subsequent that was supposed to close in the first thirty days. The reply, when it comes, is word for word what it was in month two: "we are in the process of..." Every so often a founder goes further and calls what we agreed to immaterial. If it was immaterial, why did we agree to it? Usually because closing conditions get signed in a hurry to get the round done, then quietly deprioritised the moment the money lands.
Part 1: Before the First Board Meeting was about the weeks between a term sheet and a closing, and what they reveal before anyone opens the financials. This one picks up where that left off: the six months after the wire clears, when the real innings begins.
Closing the round doesn't close the conditions subsequent. It just changes who's watching. CS items don't lose relevance because months have passed, if anything the opposite. An investor who chased hard during diligence and then goes quiet isn't disengaged; they're watching whether what was promised gets done without being asked twice. Founders who clear CS items early, unprompted, are making the same statement: what gets agreed to gets honoured.
A good finance hire earns their keep the day they tell the founder no. Hire or outsource matters less thanwhether there's a finance professional who understands regulatory and taxcompliance well enough to keep the company clean, and who has the standing topush back when governance says one thing and convenience says another. Iinterview these candidates myself before a company hires them, this is the onehire where "we got along well" isn't sufficient screening.Banking hygiene is the same test in miniature. I once had a founder ask, withcomplete sincerity, why he needed two signatories when he could sign all thecheques himself. That question told me everything about what he actuallythought of controls and governance.
Whatever got a company through its first eighteen months on Excel and a family CA rarely survives what comes next. Moving to Zoho Books, or equivalent, isn't glamorous, but it's the difference between numbers a CFO can trust, and numbers rebuilt from scratch every time someone asks. The audit relationship needs the same upgrade. I once asked an auditor why a company was recognising revenue on receipt as opposed over the duration of the service, and got back: "but the company did not give me the information to make this assessment." That single line told me the most basic judgment in the financial statements had never been tested, opening a rather large Pandora's box about what else hasn't. A small local firm chosen for cost, or family connection, was probably right pre-funding. It's rarely right once there's real accounting judgment or institutional capital to explain.
The best MIS templates get built together in month one, before either side is frustrated about what "monthly reporting" was supposed to mean. Founders who ask what the board needs, rather than what looks impressive, tend to have far more productive board meetings than the ones who don't.
The ESOP pool that was a verbal promise before the round needs to become a properly constituted scheme now. Part 1 talked about a promise to an early advisor, never written down, coming back to bite a cap table during diligence. The fix, post-closing, is getting the scheme documented, board approved, and the pool actually carved out. Doing this in month two is administration. Doing it eighteen months later, when someone finally wants to exercise, is a scramble.
Policies written after something goes wrong are apologies. None of it needs a compliance manual on day one, just the basics done properly: HR covering offer letters, POSH, and leave plans; a governance framework for delegation of authority; a finance approval matrix that isn't "ask me directly"; and enough on AML, KYC, and ESG to survive a diligence questionnaire. AML and KYC get underweighted most, founders assume it's the fund's problem, not realising it becomes their own the moment a customer or later investor asks for it, usually with a deadline attached.
And the operational milestones agreed at the table don't get a grace period either. Founders can do the same thing batsmen do after reaching fifty, ease off and start protecting the milestone instead of pushing for the win. Treating the raise as the achievement rather than the start is the tell. The ones I enjoy working with most are the opposite, constantly pushing our investment team for introductions and market intel, not the ones who only pick up when the board meeting is on the calendar. Raise mode has a particular urgency. Build mode needs a quieter version of the same hunger, easier to spot once the applause dies down.
None of it, on its own, decides anything. Not a CS item, not a missing signatory, not an audit firm asking the wrong questions. What decides it is whether the discipline shown during diligence turns into a habit, or was only ever a performance built to last as long as the round.
The founders who get remembered well aren't the ones who sail through the first six months without a single thing slipping. Nobody does. They're the ones still batting to win in the second session, not just protecting the score.
That's the throughline: the small, unglamorous moments that quietly decide how a company is read, long after the pitch is forgotten. Next up: the first year in full, and where board dynamics most often start to shift. Follow along if you'd like the next one when it's out.
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