
Partner Venture Capital Special Situation Fund @23mile | Host, 23mile Podcast (Tech M&A and Turnaround Stories)
London
Joined March 2009
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Kayode retweeted
If customers won't buy your stuff, try asking what they would buy. This sounds obvious, but surprisingly few founders do it, and it often yields valuable insights.
Granola is a proudly UK founded business 🇬🇧 So when we started planning the next season of events in London, I kept coming back to the iconic businesses built here, and the people behind them.
Really excited to be hosting the founders and makers of fabric (yes, that nightclub 🪩), @davidmelloruk (the makers of the Granola spoons 🥄) and @StarlingBank (one of the pioneers of digital banking).
Announcing the first Made in the UK line-up:
- 14 September: @AnneBoden, founder of Starling Bank, in conversation with @mattjackrob (co-founder of GoCardless, now a partner at Accel)
- 21 September: @camleslie1, co-founder of fabric, with our very own Jonathan Fialka
- 8 October: Corin Mellor, Creative Director of David Mellor, with our very own Sam Garson.
RSVP links are in the comments on the @meetgranola post!
Kayode retweeted
One of the great challenges for British start-ups has been selling to our own Government - until now.
Gov procurement has often discriminated against innovative new British companies. @UKSovereignAI has set out to change that, and after a lot of work, we've just launched our rapid procurement scheme - the first of its kind in the UK.
This is £100M of contracts for British AI companies to deliver services to make our public services cheaper and more efficient.
This scheme is designed around the needs of start-ups: No turnover minimums. Departmental champions from day 1. Upfront payments. Streamlined applications. You keep your IP.
We are launching with four initial schemes, with more to come later this year.
These are:
- Providing AI for a more productive NHS
- Integrating AI across Defence environments
- Making public compute more efficient
- Safe adoption of AI agents.
If you think you might bid for one of these, you can first check your eligibility and learn more about the schemes on the website below
sovereignai.gov.uk/compute-s…
Kayode retweeted
Replying to @yuanyi_z
It's a fascinating place, actually. The real black box is Brunei. My professional focus is Southeast Asia and I can count on one hand the number of pieces I've published on it in 5 years.
Kayode retweeted
It's story of how the proverbial VC cookie crumbles
Raise funds >> spend massively >> grow fast >> raise again
For Nick's startup, growth slowed and that's where the problems began
Kudos to him and team for taking the hard path and getting to profitability
More venture backed founders should do this instead of shutting down good businesses
One of the worst times at Gainsight ended up creating one of the best times:
In 2017, we had gone from "hot" to "not" (H/T to my friend @jhong!)
Our early days were on the path for fast growth at the time:
2013: $1M ARR
2014: $5M (5X)
2015: $16M (~3X)
2016: $30M (~2X)
In AI times, that ramp happens in a month, but that was solid traction for that era.
The problem was we were TAM constrained (primarily selling to tech companies). So our new logo bookings flattened out and in 2017, we ended at $48M. Deceleration was upon us.
Morale dropped. Our head of sales (who was a great person) resigned. A lot of his hired in people did too. I did the usual CEO thing and said "MORE LEADS!" to my CMO @akennada, but if you are out of TAM, you are out of leads.
And we were burning money like we were still in hypergrowth land. So we needed cash. We went out to raise our next round. Our pitch was basically "yes we decelerated... but give us more money and ... profit!" OK it was more artful than that, but not much. We had some ideas of new things we could do, but no evidence to support the ideas.
We called all of the VCs who for years had been "huge fans" and said "we'd love to be in business with Gainsight." My guess is we pitched 50 firms. And we got 50 NOs.
Worse still, these weren't the early stage nos where people sometimes pass because they don't know who you are. These investors passed knowing exactly who we were!
It was a brutal time as a leader. I had to get in front of the company and bring us together, while I had almost no confidence internally.
Then something lucky happened. Because we couldn't raise equity capital, we instead raised a small amount of debt. And since we had debt, we needed to get to breakeven pronto.
Our retention was good, so all we needed to do was keep growing modestly and not hire anyone. I became a nightmare to every leader and manager at Gainsight. No new hires. No backfills. End of story. Not a good way to run a company long-term (lots of problems come from this approach). But in a year and a half, we were within spitting distance of breakeven.
And because we had that profile, we were in the zone for Private Equity firms at the time (near-breakeven, good but not hypergrowth, good retention). That eventually led to Vista Equity Partners buying the company at the end of 2020 for $1.1B. Our last venture round was ~$500M and most were way below that, so everyone was happy.
Strangely, in the multiverse, Many Worlds, Sliding Doors alternate reality, we raised that last round (ironically it would have been our Series "F"!) at a $1B+ valuation, we didn't get disciplined, we later had to do massive cuts, and we were probably a zombie company with no exit.
Now would it have been better still to have had hypergrowth, gone public and be worth $100B or whatever? Sure. But for me, the story shows that sometimes failures beget successes.
Kayode retweeted
Replying to @dhippo78 @technextdotng
Great question
I have a friend who needed to build a large factory to process and package peanuts for the Nigerian market
He raised some equity but was convinced he could go big so went to the bank
You know Nigerian banks don't fund new projects right?
But this guy is connected enough and got the Abuja bank MD to directly get involved and got a $5 million loan at preferential rates
Built the factory, launched with fanfare and...
Crickets
Utilisation was 10% after 12 months... he was so focused on the impact story of this plant that he hadn't done a proper homework on demand
Oh, did I mention that the bank got comfortable to lend the money because he provided a personal guarantee backed by two of his dad's Ikoyi properties
You know what happened next
Business failed >> bank called the loan (MD stopped picking calls >> bank seized manufacturing plant + personal properties
That is uncertain growth. And banks almost never lose money on a portfolio basis so they're fine
Now, what's contracted, good debt?
MTN Group is buying IHS... reversal of deal done 10 years ago.
Those initial Tower deals were funded by debt and banks were scrambling for them. Why?
MTN spun off towers into an entity >> immediately signed 10 year contracts with fully owned entity >> sells off tower entity to IHS and other Tower operators in different countries >> operators raise debt easily because of contracted cashflow from MTN
Two young companies raising debt, two totally different profiles
Kayode retweeted
Only 2% of startups ever get acquired, Jessica Christiansen-Franks scaled the startup she accidentally founded with her then boss to a remarkable exit to an Australian listed proptech giant in just 8 years.
Watch the full episode
youtu.be/wTXbOqBjexA
Kayode retweeted
Jessica Christiansen-Franks accidentally founded a startup, then sold to $25bn proptech giant in just 8 years.
Through all the ups and downs, including Covid, she says it was fucking fun.
See full episode
youtube.com/shorts/8x3y1jZyT…
@Kayodeodeleye
Kayode retweeted
A lot of people think that Harvey is like, ChatGPT for legal or something.
The outside world has no idea about the extreme product velocity at Harvey, nor about the product direction or long term product vision.
We’re trying to share more here. Eng is cooking
Kayode retweeted
We cannot consider #AI to be morally neutral. In reality, every technical tool embodies choices and priorities through what it measures, ignores, and optimizes, and how it classifies people and situations. Ethical discernment cannot be limited to asking whether we are using a system for good or bad purposes. It must also examine how that system is designed and what vision of the human person and society is embedded in the data and models that guide it. #MagnificaHumanitas
Kayode retweeted
It’s remarkable how much of life is about finding something to work on that gives you energy and surrounding yourself with people you love and then ruthlessly and militantly blocking out every single thing that gets in the way of maximizing your time spent on those two things
Kayode retweeted
The Obama Presidential Center is finally opening!
Tune in today on Obama.org starting at 11am CT as Michelle and I share what this moment means to us and celebrate with friends, family, and members of the community in Chicago.
Kayode retweeted
Great content does one of three things:
1. Teaches something you did not know.
2. Educates you on something you thought you knew but you were wrong on.
3. Tells you a secret/miracle that changes everything you previously thought.
Kayode retweeted
Many CEOs make million $$$ decisions on AI usage for their firms without
1) understanding what AI can and can't do
2) what parts of their workflow are best automated and which to leave human-led
And so we're left with them desperately paying for help from consultants...
Kayode retweeted
This is an example of a task that would take a few hours in my days as an investment banking junior
Converting PDF historicals into a well formatted financial model format before then building out the projections
Claude 4.8 got it in one shot
Kayode retweeted
The older I get, the more I realize that optimism is a competitive advantage. Not blind positivity. The belief that problems can be solved. That things can improve. That your actions matter. People who believe a better future is possible are the ones who create it.
Kayode retweeted
Here you go. This task that would take a few hours in my days as an investment banking junior
Converting PDF historicals into a well formatted financial model format before then building out the projections
Claude 4.8 got it in one shot
One of things I cover in weekly AI in finance newsletter. See below
kayfin.co/financeupturned04
Kayode retweeted
See full issue and don’t forget to subscribe
kayfin.co/financeupturned04



























