Kayode

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Kayode

Kayode

@Kayodeodeleye

Partner Venture Capital Special Situation Fund @23mile | Host, 23mile Podcast (Tech M&A and Turnaround Stories)

London Katılım Mart 2009
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Kayode
Kayode@Kayodeodeleye·
If I knew what I knew now, I wouldn't have raised venture capital." This is what a founder friend told me the last time we caught up. Two big headaches he's facing: 🥵 sheer weariness from fundraising every year for the past 12 years ❌ constant challenge of meeting sky-high targets after his recent growth equity round And he's one of the lucky ones who has taken some "chips off the table." The fact is that for many founders, the VC path becomes a death spiral, leaving them broken with nothing to show for it That's why we've put together a framework to help founders think through their options and escape the VC hypergrowth model Give it a read if you're on the venture path, thinking of it, or just want to know how venture really works💡 Details below 👇🏽 @23milecapital
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Kayode
Kayode@Kayodeodeleye·
What's the secret to an 8-figure exit? According to Amber Vodegal "the sacrifice you need to make is do not watch TV. If you want to set up a business, the first thing you do is limit your TV evenings to one or two X a week maximum" youtube.com/shorts/y18PuFN…
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Kayode
Kayode@Kayodeodeleye·
Startups failing is a really sad thing But when very high profile startups flame out, there's always a thing or two to pick from their rise and fall 1️⃣ Debt is a double-edged sword, Parker raised over $200 million in funding, including around $140 million of debt 2️⃣ Blitzscaling is betting the house. You increase your chances of failure but if you succeed you hit it big 3️⃣ A deal is not done until cash hits the bank. Parker went from live acquisition talks to complete liquidation within a few weeks 4️⃣ An M&A deal with your backs to the wall is really a distress deal. Getting into acquisition conversation without viable alternatives - other buyers and continuation as going concern - is just wild 5️⃣ Startups are risk, startups fail all the time but founders never fail The founders will def bounce back
Yacine@YacineSibous

Well, that was a crazy turn of events. Three weeks ago, I thought Parker was going to be acquired in a deal worth nearly $90M. Yesterday, we filed for Chapter 7. I spent most of my twenties building Parker. We went from an idea in YC to processing over $1B in annualized volume, pioneered products that became standard across fintech, and built something I believed could last for decades. And now it’s over. I know there’s going to be speculation about why Parker failed, but a lot of what’s being said online is simply not accurate. Over the last few years, we faced leadership turnover, a much tougher market, slowing growth, and the realities of trying to scale a venture-backed business after momentum fades. Earlier this year, we decided the best path forward was to pursue a sale of the business. We ran a process and spent months working toward a potential acquisition that ultimately did not close. After that, things moved quickly. The hardest part is the impact on the people involved: •Customers dealing with disruption •Employees losing jobs they worked hard for •Investors who believed in us losing money What I am proud of is the team. Parker was built by incredibly talented people who deserved a better outcome than this. Helping them land somewhere great is my top priority right now. If you’re hiring operators, engineers, designers, finance, credit, or growth talent, please reach out. To everyone who believed in Parker over the years: thank you.

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Kayode
Kayode@Kayodeodeleye·
How Amber Turned a Side Hustle into an 8-Figure Exit 🔥 She built apps in the evening after tucking her kids into bed while working a full time job This brutal situation went on for years but it all worked out beautifully @AmberVodegel sold Pregnancy+ to Philips in a life-changing exit and and kept almost 100% of the proceeds as she was bootstrapped After a stint scaling the app massively within Philips and a short mini-retirement, she's back building 28X, a free women's health app for the 80% who can't afford subscriptions Episode 20 of 23mile is live now 🔥 kayfin.co/23milepodcast20 #acquisitions #entrepreneurship #founders #bootstrapping
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Kayode
Kayode@Kayodeodeleye·
She worked 7pm to 11pm every night while her kids slept. Built three companies before one sold to Philips for 8 figures Episode 20 of 23mile is now live youtu.be/wcy281RmT8w
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Kayode
Kayode@Kayodeodeleye·
@lkr 💯 London also has the advantage that finance is big and they make tons of money Everyone is fine with and used to it No need to brag like you said
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Laura Roeder
Laura Roeder@lkr·
London has entered the chat. London has the expensive thing going for it, you simply have to think larger if you're going to live off your business in London. And while it's true that British culture doesn't exactly embrace entrepreneurship, London has its own thriving subculture that does. Bragging is very looked down upon, so it doesn't have that cheesy fake hustle culture of the US. And that just gives the whole thing this vibe that's more playful. People are way more open and willing to share what's going wrong. Does it have the SF ambition? No. But it has a fun drive and energy, and it's easy to surround yourself with people building great businesses without all the BS.
@levelsio@levelsio

The only 2 places where I felt ambition like this are the US and China Nomad hubs like Bali and Thailand are nice but often people there get stuck coasting at $5K MRR because it's just cheaper to live there, so that puts kind of a natural limit on ambition, very quickly you already make "enough" SF/NYC are so ridiculously expensive to live, so you HAVE to make a lot of money, and the high cost of living is a natural filter that keeps only broke but super ambitious or already successful people (and of course nepo babies esp NYC) China is not so much expensive to live, but there's some natural cultural ambition to become #1 in everything that's very infectious

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Patrick OShaughnessy
Patrick OShaughnessy@patrick_oshag·
Anyone read anything really great lately (any format)?
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molson 🧠⚙️
molson 🧠⚙️@Molson_Hart·
@Kayodeodeleye I used to fight it more. This is kind of my white whale. Also I’m trapped in it remember? They’ve sued my company as well.
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molson 🧠⚙️
molson 🧠⚙️@Molson_Hart·
After the publishing of this article, my company was sued in bankruptcy court. That case was just dismissed along with 2nd bankruptcy. So now we are returning to district court for the 4th time in year 8. Situation is getting so interesting that we might need a part 2!
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molson 🧠⚙️@Molson_Hart

x.com/i/article/1993…

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Kayode
Kayode@Kayodeodeleye·
@Molson_Hart Damn! Tbf, you must be nuts I fought injustice at a scale 1% of this and only endurance running saved me. I gave up after 4 years and moved on with life We’re rooting for you, don’t give up 🫣
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greg
greg@greg16676935420·
This might be a stupid question but how do people who wear glasses find their glasses when they misplace them
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Kayode
Kayode@Kayodeodeleye·
AI is eating the world but I’m betting on some things to be more in demand * storytelling * in person events * bespoke and personalised services Humans love humans
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A Finance Guy’s Ex-Wife
$1M in the stock market: roughly $80k a year if everything goes right. $1M in a boring business: $250-300k+ a year after debt service. $1M in a wedding with a high performing HBS (Harvard Business School) graduate early in his career with an exit after ~5 years and one one kid: $10.2M and $55k a month in alimony and child support. Same starting capital. 3-4x the result. Why aren’t more people doing this?
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Kayode
Kayode@Kayodeodeleye·
@c20h10n2 @Brady_H BMI is definitely not it. The whole convo is more complex than you’re making it out to be. I’ve run full marathons at 95kg, 14% body weight. Running was pleasurable. I’m 6’3 and big boned. So it’s not a simple equation
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Jennifer
Jennifer@c20h10n2·
@Brady_H Then what is the right weight by gender/height/age, because BMI is NOT what's up
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Alex Lieberman
Alex Lieberman@businessbarista·
I want to start an AI community for executives. This will be a space for people to share killer use cases, agentic workflows/agents, post-AI org structure, AI governance, AI training/enablement, change management, and more. Comment “AI-native” if you want to join.
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