I was speaking with a friend who’d recently come out of a breakup and was diving into the deep end of Dubai dating.
He had every app known to mankind, including one I’m fairly sure was a crypto Ponzi scheme with a dating component. (Welcome to Dating in Dubai in 2026)
It was Friday afternoon. He had three matches he was talking to, four hours until the evening, and no concrete plans.
His solution was to suggest a time and a place to all three. Whoever confirmed first would be his Friday night.
I’ll leave the relationship advice to someone with better qualifications. But he had identified something useful: three promising conversations still hadn’t given him anything to put in his calendar.
A fundraising spreadsheet can look remarkably similar.
Five investors marked “interested.” Two have the data room. One wants another call. Another said the business fits exactly where they think the market is going.
There is enough encouragement to tell your co-founder the round is moving. Enough work to keep you occupied answering questions. And enough ambiguity that, three weeks later, you can find yourself giving almost exactly the same update.
“We’re having some really good conversations.”
You might be. The question is what those conversations are moving towards.
One word, two jobs
The difficulty is that “interested” can be an entirely honest answer.
An investor can like your company, believe the market is attractive and enjoy speaking with you, while still being some distance from deciding whether to invest.
Moving forward means doing work. Someone has to examine the business, involve colleagues and build a case they’re willing to defend. Keeping the conversation open lets them learn more before making that commitment. Another month might bring a signed customer, clearer numbers or progress elsewhere in the round.
From their side, waiting can be reasonable. From yours, five conversations like that can fill a month without bringing you much closer to funding.
That’s where the same word starts doing two different jobs. The investor uses “interested” to describe a willingness to keep looking. The founder puts it in a spreadsheet and starts planning around the possibility of a cheque.
So what makes an investor stop looking and start deciding?
Where real urgency comes from
A deadline you set because your runway is short creates urgency for you. It doesn’t, by itself, give an investor a reason to decide sooner.
What changes their calculation is the possibility that waiting will cost them an opportunity they actually want.
That is difficult to create when your investor conversations are spread across three months. By the time the fifth investor understands the business, the first has gone quiet. You keep starting conversations without bringing enough of them towards a decision at the same time.
My friend didn’t message one match and wait a week to hear back before trying the next. He sent the same time and place to all three.
This is where sequencing matters.
Book first meetings within a concentrated window. Move the promising conversations forward in parallel. Find out what each investor needs, get them the relevant evidence, and agree on next steps while the other discussions are still active.
You can’t make every fund work at the same speed. You can avoid running the entire raise one investor at a time.
As those conversations advance, communicate what has actually happened. An upcoming partner meeting is an upcoming partner meeting. A term sheet is a term sheet. Neither should be described as money committed.
The distinction matters because interest from elsewhere becomes useful information only when investors believe your account of it.
And they still have to want the company. Five simultaneous conversations won’t rescue an investment case nobody believes in. But if there is genuine interest, a coordinated process gives it a better chance of becoming a decision before everyone settles into waiting.
Investors talk to each other. Your urgency is only as strong as their belief that it’s real.
Moving each conversation forward
Running conversations in parallel only works if you know what each one is waiting for.
Look at what might sit underneath those five names.
One wants to see whether your pilots convert. Another likes the business but hasn’t discussed it with their partners. A third might participate once someone else leads.
Those are three different situations, even if all three meetings went well.
Before sending another “just checking in,” I’d want answers to three questions:
Who is moving this forward internally?
Unclear: “The team really likes it.”
Workable: “Sarah is presenting it at Monday’s partner meeting.”
What remains unresolved?
Unclear: “We’d love to see how things develop.”
Workable: “We need to understand whether enterprise customers renew.”
What happens after that is resolved?
Unclear: “Let’s keep in touch.”
Workable: “After the reference calls, we’ll decide whether to progress to a partner meeting.”
None of the workable answers guarantees an investment. They tell you what the next piece of work is meant to accomplish.
Titles alone won’t tell you who matters. An associate actively building support can be more useful than a partner who enjoyed the meeting and has done nothing since. Find out who else needs to be convinced.
Once you know what’s holding an investor back, give the next conversation a purpose. My friend suggested a time and a place, which gave the people he was talking to something concrete to respond to.
If the renewals haven’t happened, better wording won’t supply the missing evidence. Agree when to reconnect and get back to producing it.
Look at the five again
You should now be able to describe each conversation more precisely: a next step that’s underway, progress that depends on a defined condition, or a path forward that’s still unclear.
You might end up with one active process, two conversations worth revisiting after a milestone and two you understand less well than you thought.
That can be uncomfortable when you’ve been telling yourself there are five investors in play. But it also reveals the real “interested” parties to focus your energy on.
For all the readers that made it so far, here’s the real pay off regarding my friend’s friday night.
One of the three did reply.
She suggested a different restaurant. Closer to her. Considerably further from his budget.
He went. The bill was much larger than he’d planned, and the evening didn’t lead anywhere.
A confirmed plan, it turned out, still left him with a decision to make.
There’s a fundraising lesson in that too. When one investor is the only person moving, it becomes easier to accommodate another request, accept another delay, or entertain terms you would have questioned a month earlier.
You’re relieved something is happening. That can make it harder to judge whether what’s happening works for you.
So once you’ve worked out which of your five investors is actually progressing, ask yourself one more question: would I be as comfortable with this conversation if two others were moving too?
Sorry for outing you like that James (permissions were asked). Drinks are on me. Somewhere considerably less fancy than last Friday though.
Clipped
Humanoid robots walked the runway for the first time at the Milan Fashion Show and they said Italian’s don’t do innovation.
One Question
What’s the vaguest “next step” an investor has given you, and what do you think it actually meant?
Reply and tell me. I’ll share the best ones (anonymised) in a future issue, with a translation from the other side of the table.
Written from the other side of the table.
P.S. If you’re sorting through a pipeline like this for your own raise, reply and we can go through it together.