4x Founder - 1 Exit | Business Coach & Technology Executive | Deep in AI & Web 3 | Digital Transformation

I’m a 4× founder with an exit, ventures launched in Hong Kong, Switzerland, Spain, and the UK, and millions raised from US and European investors. I’ve negotiated hundreds of millions in enterprise deals and joined Streamr during its early scale-up, leading Marketplace, Partnerships, and Labs as the company grew from 5 to 30+ people following a $32M raise.

In the past 12 months, I’ve mentored 24 startups — several backed by leading VCs including Antler and accelerators such as Outlier Ventures. Tech is the common thread; sectors span AI consulting and development, robotics, education, construction, shipping, surveillance, oceans, agriculture, law, infrastructure, and finance. The work is hands-on: weekly or bi-weekly cadence, direct feedback, and execution sprints.

In 10 years of business coaching, I’ve sustained a 4.9/5 satisfaction rating from my mentees — built on candour, trust, and consistent results.

My approach is deliberately contrarian: first principles over playbooks, customer proof over pitch theatre. ClearPath (see my coaching website) is the product of that experience — a practical diagnostic that maps where a company is now, defines what’s blocking growth, and turns it into a focused plan. Then I help implement it on a fractional basis until results land. That’s how I’ve helped multiple companies reach millions in ARR, four of them within 16 months of launch.

When needed, I drive hard pivots. After raising $2.2M for Silta v1 (tokenisation) and missing PMF, I pivoted the company to AI, secured seed grant funding from the Asian Development Bank — a multilateral with $150B+ in assets — and led it to $1M ARR within 12 months.

Results with mentees: four companies hit $1M in revenue within 16 months; two others doubled revenue in under a year; one turnaround from near-collapse to profitability in four months; a sales portfolio scaled from $5M to $22M in two years. I speak at Google HQ, the UN, and the World Economic Forum on technology, innovation, and systems change.

My son just told me he prefers quantity over quality.

So I asked, “Would you rather have five chocolate bars you don’t like, or one you really love?”

He said, “I’ll take the five I don’t like — I can trade them for ones I do.”

It made me smile. But also… that’s market thinking in action.

He’s already figured out:
	•	how to turn surplus into value
	•	how to find demand where others don’t
	•	and how to use trade to get what he wants

Not bad for an nine-year-old.

Ben Sheppard

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4x Founder 1 Exit, 12 yrs Board Director, Fractional Operator & Startup Coach Seed–Series D | Scaling, Turnarounds

The 5 Silent Killers of Startups 👇

They don’t show up on your P&L — until it’s too late.

1️⃣ Overspending when cash is good.
2️⃣ Building a company that revolves around you.
3️⃣ Sales and delivery speaking different languages.
4️⃣ No operating rhythm or shared scoreboard.
5️⃣ Handovers that leak trust, time, and cash.

I’ve seen these patterns destroy brilliant teams — and they’re all fixable with the right clarity and structure.

That’s what my ClearPath Diagnostic Framework was built for.

💬 Comment 𝐂𝐥𝐞𝐚𝐫𝐏𝐚𝐭𝐡 below and I’ll send you the framework I use with founders to find — and fix — these blind spots before they kill growth.

Last week in Geneva, standing outside the UN building, I realised something I’ve known for years but often forget: 

The moment I step away from the desk, my thinking sharpens.

It’s almost embarrassing how predictable it is. Change the environment and ideas that refused to budge suddenly unlock themselves. 

The harder you push at a problem, the more it digs its heels in — but give yourself space, and the answers turn up quietly.

It’s followed me through every company I’ve built.

I can still picture myself in General Santos Fishing Port in the Philippines, toes in the sand, wondering how to scale my second startup.  Weeks of grinding produced nothing.  One afternoon on the beach produced the entire expansion plan into Indonesia and Malaysia.

The same pattern showed up in Vietnam with Silta Finance. We were pushing a dead-end product direction. Stress everywhere. But the insight that changed our trajectory didn’t come from a meeting room — it came the moment I stepped away and let my mind breathe.

And it’s happening again now with my clients. New features, new angles, cleaner offers — none of it arrived while hammering a keyboard. It arrived in the gaps.

Founders don’t always like hearing this, but it’s true: if you stay chained to the desk, your creativity collapses. When creativity collapses, your edge disappears. And once your edge is gone, your business drifts.

One thing I’ve learned working with Envoqe is that thinking time isn’t indulgent. It’s a strategic advantage. When you change your scenery, you change your decisions.

Your mind works best when you give it room.

Over the past couple of weeks, a few conversations with founders, investors, and deep-tech teams have stopped me in my tracks — the kind that quietly signal where things are heading.

In today’s newsletter, I’m unpacking the themes that keep resurfacing:

🔹 Forward-Deployed Engineers (FDEs) — why they’re suddenly everywhere again, and how they’re changing the way software development and consulting companies go to market.
 🔹 Full-Stack AI companies — YC’s big push, and what it really means to “own the whole problem.”
 🔹 Yann LeCun stepping away from Meta — and what this might signal about the next creative wave in AI.
 🔹 A clean-room scenario founders must understand — especially if you’re selling into enterprises.
 🔹 The five silent killers that quietly undermine startups — patterns I see repeatedly in coaching sessions.
 🔹 A spotlight on WeBetterAI — two brilliant founders building at the pointy end of AI, quantum, and nanotech.

And on a personal note, I’ve spent the past six weeks experimenting with fasting alongside my HYROX training… with some surprising lessons in focus, discipline, and energy.

If you want to read the full breakdown, here it is 👇

A Note Before We Begin The past couple of weeks have been full of conversations that stuck with me — the kind that quietly signal where the industry i

Open article: Signals From the Edge: Trends, Clean Rooms, and What’s Quietly Reshaping Startups by Ben Sheppard • 9 min read

Signals From the Edge: Trends, Clean Rooms, and What’s Quietly Reshaping Startups

𝐄𝐯𝐞𝐫𝐲 𝐟𝐨𝐮𝐧𝐝𝐞𝐫 𝐭𝐡𝐢𝐧𝐤𝐬 𝐭𝐡𝐞𝐲’𝐫𝐞 𝐭𝐡𝐞 𝐞𝐱𝐜𝐞𝐩𝐭𝐢𝐨𝐧 — until these 5 blind spots catch up with them.

They don’t show up on your balance sheet until it’s too late.

In my work with founders, these 5 patterns cause 90% of the chaos, wasted cash, and burnout I see.

👉 Comment 𝐂𝐥𝐞𝐚𝐫𝐏𝐚𝐭𝐡 below and I’ll send you the full ClearPath Diagnostic — the framework I use to help founders double revenue or stabilise fast.

5 Blind spots that quietly kill startups

A founder came to me running two tech products at once. 
On paper it looked ambitious. In reality, both companies were suffocating.

One product had early traction but had completely stalled.
The other had flashes of potential but couldn’t grow because the team was constantly switching context, losing depth, and firefighting across both worlds. Everyone was working hard, but no one was working effectively.

This situation is far more common than people think.

Founders convince themselves they’re “diversifying.” What they’re actually doing is splitting their focus, diluting their team, and quietly starving both companies of the attention required to win.

When we started working together, I told him something brutally simple:
“If you keep building two companies, you will lose both.”

So we ran my ClearPath assessment — a deep look into both startups, the operations, the financial health, the execution cadence, the product signals, and the real bottlenecks. 

Then we applied a handful of quick-win tests to each business to see where the opportunity truly lived.

The results were immediate.
One product responded.
The other didn’t move at all.

That gave us the answer people often avoid: one company needed to die so the other could live.

The founder made the call — not easily, but decisively.

The moment the team focused fully on the stronger product, momentum returned. You could feel it. Pipeline deepened. Work quality lifted. Decisions became clearer. The whole company started breathing again.

But there was a second layer to deal with:

Some team members simply couldn’t adapt to real focus.
They were used to working “part-time” on each startup and suddenly couldn’t recalibrate when asked to give one company their full attention. That mindset costs more companies than bad strategy does.

We made changes.
We redesigned the operating model.
We removed the people who couldn’t shift gears.

And we rebuilt parts of the workflow with systems and tools that removed friction.

Eighteen months later, that startup has tripled its revenue — and it’s more profitable than it has ever been. Not because we chased growth blindly, but because we built a business that could grow with clarity, focus, and discipline.

The lesson is brutally honest: you don’t scale by adding more.
You scale by removing what drags you backwards.
Focus isn’t a luxury.
It’s a competitive advantage.

Always appreciate hearing from the people I work with.
Andrew left this ⭐️⭐️⭐️⭐️⭐️ review on MentorCruise :

“great advice and very helpful in my journey towards sales and entrepreneurship!”

If you’re looking for support, sharper thinking, or a bit of direction as you build — drop me a message. Happy to chat.

Don’t be the moped.

I was walking my dog earlier when this tiny moped screamed past — loud enough to wake the dead, yet barely moving faster than a jogger. It got me thinking about early-stage founders.

Many sound just like that moped when pitching VCs:
- A lot of noise, not much horsepower.
- Big revs, little traction.

It’s not because they’re foolish — it’s usually inexperience and nerves. But that noise hides the real issue: no clear customer path and no believable story.

If you’re pre-revenue, your power doesn’t come from shouting louder. It comes from clarity — a credible problem, a grounded solution, and a plan to get paying customers.

So here’s the difference:
- A moped makes noise to feel fast.
- A Ferrari is quiet until it’s fuelled — then it flies.

Don’t be the moped. Be the Ferrari that just needs gasoline.

If you’re doing B2B deals with large enterprises, there’s a term you might not have heard yet, but you probably should:

“𝐂𝐥𝐞𝐚𝐧 𝐫𝐨𝐨𝐦.”

In simple terms, a clean room is a legal and process setup an enterprise can use when it wants to rebuild a product without (in theory) using your confidential information.

The basic idea looks like this:

A “read team” is allowed to look at public information about your product – your website, marketing materials, public talks, patents, documentation you’ve published.

A separate “build team” is then kept “isolated” and asked to recreate similar functionality based only on what the read team says they learned.

On paper, this is meant to keep the process clean:
“We only used public info, so we didn’t copy anything proprietary.”

In reality, it gets messy when the enterprise has already:

run pilots with you,
seen deeper parts of the product,
had technical walk-throughs,
or received confidential materials under NDA.

𝐘𝐨𝐮 𝐜𝐚𝐧’𝐭 𝐮𝐧𝐬𝐞𝐞 𝐭𝐡𝐚𝐭.

Once an organisation has had that level of access, claiming the end result is based purely on “public information” becomes very questionable.

I’m seeing this pattern more often as big companies get more confident in AI, internal build teams, and “we can do this ourselves” thinking.

If you’re selling into large organisations, you don’t need to be paranoid – but you do need to be structured and deliberate about:

what you show,
when you show it,
and what your contracts actually say about reverse engineering and derivatives.

I’ve recorded a short video walking through this in more detail and what founders can do to protect themselves. If you want help understanding this more deeply, DM me. 

👇 Watch it here.

There’s a myth that founders are natural leaders.

I wish it were true. But most of us learn the hard way.

You start out thinking it’s about vision, strategy, maybe a bit of charisma. Turns out, it’s mostly about listening. And apologising. And learning to let go of things you thought only you could do.

I’ve made every leadership mistake in the book. Micromanaged. Avoided hard conversations. Tried to fix everything myself.

The turning point? Realising that people don’t want a superhero. They want someone who’s honest about what’s hard, and who shows up when it matters.

If you’re a founder struggling with the people side, you’re not broken. You’re just learning in public.

Keep showing up. That’s what makes the difference.

This little legend is coming to work with me in Barcelona today.

She normally supervises from the home office, but today she’ll be joining the meetings at with Sarah Taylor at Envoqe.

There’s something about having your dog curled up under the desk that just changes the whole energy of a workday. A bit of calm. A bit of mischief. And a reminder not to take any of it too seriously.

Do you take a pet to work?

Drop a comment — and show me a photo of your favourite work buddy. I want to see the characters you’re building companies with.

Founder | Spatial Intelligence and Cognitive Performance | Environments of Stillness | ANFA Spain | ANFA UK

Envoqe

The 5 Blind Spots That Quietly Kill Startups 👇

They don’t show up on your balance sheet — until it’s too late.
Over the years I’ve seen founders burn through millions and others stall just as things were getting good.

Not because their idea was wrong, but because of what they couldn’t see coming.

Here are the five blind spots I see most often:

1️⃣ 𝐘𝐨𝐮 𝐨𝐯𝐞𝐫𝐬𝐩𝐞𝐧𝐝 𝐰𝐡𝐞𝐧 𝐭𝐡𝐞 𝐦𝐨𝐧𝐞𝐲’𝐬 𝐠𝐨𝐨𝐝.
 When cash is flowing, discipline disappears.
 Most founders forget to plan for the season when it doesn’t.

2️⃣ 𝐓𝐡𝐞 𝐛𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐫𝐞𝐯𝐨𝐥𝐯𝐞𝐬 𝐚𝐫𝐨𝐮𝐧𝐝 𝐲𝐨𝐮.
 Every decision, sale, and delivery runs through the founder.
 When you’re the system, growth breaks the system.

3️⃣ 𝐒𝐚𝐥𝐞𝐬 𝐚𝐧𝐝 𝐝𝐞𝐥𝐢𝐯𝐞𝐫𝐲 𝐝𝐨𝐧’𝐭 𝐬𝐩𝐞𝐚𝐤 𝐭𝐡𝐞 𝐬𝐚𝐦𝐞 𝐥𝐚𝐧𝐠𝐮𝐚𝐠𝐞.
 Either the sales team sells what can’t be built,
 or the builders create what no one sold.
 Both kill margin and trust.

4️⃣ 𝐓𝐡𝐞𝐫𝐞’𝐬 𝐧𝐨 𝐨𝐩𝐞𝐫𝐚𝐭𝐢𝐧𝐠 𝐫𝐡𝐲𝐭𝐡𝐦.
 Teams meet, but don’t align.
 No shared scoreboard.
 No accountability.
 No momentum.

5️⃣ 𝐓𝐡𝐞 𝐡𝐚𝐧𝐝𝐨𝐯𝐞𝐫𝐬 𝐥𝐞𝐚𝐤.
 Marketing to sales.
 Sales to delivery.
 Delivery to support.
 Every gap drains trust, time, and cash.

These are the cracks I uncover in my ClearPath Diagnostic Framework.
 In just a few weeks, I help founders cut waste or scale faster — without chaos.

💬 Comment 𝐂𝐥𝐞𝐚𝐫𝐏𝐚𝐭𝐡 below and I’ll send you the full diagnostic deck — the same framework I use with founders to rebuild clarity and control in their business.

Growth rarely dies from lack of effort.
It dies from too many priorities.

This is the story of how one founder cut the noise and tripled revenue.
It might hit closer to home than you expect.

The Founder Who Tried to Scale Two Startups at Once

𝐓𝐡𝐢𝐧𝐤𝐢𝐧𝐠 𝐂𝐨𝐫𝐫𝐞𝐜𝐭𝐥𝐲 𝐔𝐧𝐝𝐞𝐫 𝐏𝐫𝐞𝐬𝐬𝐮𝐫𝐞 (𝐓𝐂𝐔𝐏) — a concept Clive Woodward drilled into England’s 2003 World Cup winning squad.

It’s something I’ve carried with me ever since — from the pitch to the boardroom.

In this two-minute video, I share a story from my first company. I was under real pressure to close a deal — desperate, even. But instead of rushing it, I paused, applied TCUP, and held my line.

That decision changed everything. 

It led to a deal with Bloomberg Philanthropies and the Rockefeller Foundation — and taught me one of the most valuable lessons in business: pressure doesn’t create character; it reveals it.

This is great advice. Finally some brutal honesty on LinkedIn.

CDO at 4th Utility | 56K+ Followers | 48 Million Impressions last 12 months | AI Leader | Venture Builder

Vinod Khosla once said something brutally honest:

“70% of investors add negative value to a company.”

When junior team members at Khosla Ventures ask to sit on portfolio boards, his answer is simple:

“You haven’t earned the right to advise an entrepreneur.”

Why?

Because building and advising aren’t the same thing.

As Khosla puts it, getting an MBA and joining a VC firm doesn’t mean you understand what it’s like to live through uncertainty, make impossible trade-offs, or build under pressure.

He believes you earn that right only by doing it yourself:

“If someone has never dealt with decision-making under ambiguity, they’re not qualified to help you.”

It’s a sharp reminder for founders too, choosing whose advice to trust is one of the hardest and most important decisions you’ll ever make.

Khosla’s examples hit the point home:

💡 A marketing exec from IBM might know how to scale but not how to invent a market.
💡 A healthcare veteran used to 2% change a year might struggle in a startup moving 200% a month.

The takeaway?

Experience isn’t the same as relevance.

In fast-changing fields, like AI, data, or emerging tech, the rate of learning often matters more than years in the game.

Maybe the better question isn’t “Who’s experienced?”

But rather “Who’s learning faster than the world is changing?”

Credit The VC Corner

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Marketing | CRM | Entrepreneur | Innovation

Turns out I’m a Lion.

Not the majestic savannah kind — more the “up before everyone else, peak early, and ready for bed long before Netflix asks if I’m still watching” kind.

Every week when I meet with Sarah Taylor  to work on the Envoqe project, she teaches me something new.

This week’s lesson: chronotypes — basically the science of when your body wants to sleep, wake, think, create, and recover.

And honestly, it explains a lot about why I’m fully functional at 6 a.m. while half the world is still negotiating with their alarm clock.

Here’s the quick breakdown:

🐁 The science bit (in plain English)

Your chronotype is tied to your circadian rhythm — the internal 24-hour clock that shapes your alertness, energy peaks, and sleep patterns.
It sits on a continuum, not in neat boxes. Some people are moderate; others live at the extremes.

🐾 The animal types (the fun version)

🦁 Lion – Early risers. Peak in the morning. Bed by 9–10 p.m.
🐻 Bear – Follow the sun. Wake with light, sleep with dark. Most common and most social.
🐺 Wolf – Night owls. Slow start, creative late, thrive when the world quiets down.
🐬 Dolphin – Light sleepers. Irregular patterns, alert brains, bursts of productivity.

🔬 The scientific categories (the strict version)

Morning type – Peak early, fade early.
Evening type – Peak late, creative and alert at night.
Intermediate – Neither extreme; more flexible across the day.

I’m very much a Lion — front-loaded energy, early focus, and happiest when the day starts before the rest of the city.

Now I’m curious what chronotype are you?

What chronotype are you?

Vote in the poll and tell me in the comments if you’ve ever tried organising your day around your natural rhythm

Your competitor just hired a $300k “Head of Strategy.”

Here’s how you still outrun them.👇

Rule 1: They’ll build slides. You’ll build customers.
Big hires need to justify themselves.
That means frameworks, planning cycles, and endless “alignment.”
While they’re aligning, you’re closing.
Speed beats polish every time.

Rule 2: They’ll chase sophistication. You’ll chase adoption.
Complex strategy feels impressive.
But the companies winning right now?
They ship simple things customers actually use.
Their roadmap is 100 pages.
Yours is five bullet points and a weekly cadence.

Rule 3: They’ll manage stakeholders. You’ll manage reality.
The more senior the hire, the more politics they inherit.
Boards. Investors. Internal drama.
You get to ignore all of that and optimise for truth, not theatre.

Rule 4: They’ll scale headcount. You’ll scale outcomes.
They celebrate hiring sprees.
You celebrate revenue.
One inflates the ego.
The other keeps you alive.

Rule 5: They’ll spend money. You’ll make it.
Strategy hires come with burn.
Pressure.
Expectations.
You’ve got none of that.
Your unfair advantage is focus, not funding.

The formula?
Do the opposite of what “big company logic” forces them to do.

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