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

I partner with funded companies (Seed–Series D) when growth stalls, complexity spikes, or the business simply outgrows its operating system. My work blends founder experience, corporate scale, and hard-earned judgment from 20+ years operating in high-stakes environments.

I’ve built four companies across Hong Kong, Switzerland, Spain, and the UK. I’ve raised $2.2M pre-product off a deck and a vision, led a hard pivot to AI, secured backing from the Asian Development Bank ($150B AUM), and grew the business to $1M ARR within the first year. Before startups, I spent a decade advising some of Southeast Asia’s most influential business families on $200M–$400M infrastructure investments, founding the companies to deliver those projects and onboarding large operational teams.

I’ve negotiated hundreds of millions in enterprise deals, run 120-person delivery teams, and scaled project portfolios from $5M → $22M. At Streamr, I led Marketplace, Partnerships, and Labs as we grew from 5 to 30+ people following a $32M raise. My consulting units have reached ~$2M ARR, and my advisory work spans AI, healthcare, mobility, deep tech, data, infrastructure, and financial services.

In the past 12 months, I’ve supported 24 startups — several backed by Antler, Outlier Ventures, and other leading VCs. Results include four companies hitting $1M+ revenue within 16 months, a turnaround from near-collapse to profitability in four months, and multiple teams doubling MRR in under a year. I help founders tighten their operating rhythm, solve complex problems, sharpen their decision-making, and navigate fundraising, GTM resets, pivots, investor pressure, and early M&A conversations.

I speak at Google HQ, the United Nations, and the World Economic Forum on AI, innovation, and systems change. My approach is straightforward: no theatre, no templates-for-the-sake-of-it, just clear thinking, honest conversations, and execution that moves the business forward.

If you’re scaling something ambitious and want steadier leadership, sharper decisions, and a partner who’s been there at every stage — let’s talk.

If you’re building an early-stage startup, you have to take risks.
You have to tear the band-aid off, go for it, and see what happens.

Failure isn’t something that might happen.
It will happen. Over and over again.
Sometimes several times in a single day.

What I see too often is founders hitting seed stage — a bit of funding, a bit of revenue — and suddenly acting like there’s something to protect.

There isn’t.

I’ve written a longer piece on this, grounded in my own experience, about why playing safe too early is one of the fastest ways to get stuck on the hamster wheel.

Ben Sheppard

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

If you’re building an early-stage startup, you have to take risks. You have to be willing to tear the band-aid off, go for it, and see what happens. Y

Open article: Too Careful, Too Early by Ben Sheppard • 7 min read

When you launch a startup, you’ve basically got nothing.

You’ve got an idea.
Maybe a prototype.
Maybe £20–30k in the bank — often your own money plus a bit of angel cash.

That’s it.

And yet I see founders acting like that money, or that MVP, is something sacred that must be protected.

Angels aren’t there to watch you play safe.
They’re there because they want that money used to springboard the company towards something that could be worth 10x.

That doesn’t come from being careful.

Read my full blog on this below: 

https://lnkd.in/d4VXWxRi

January is a good moment to sharpen the basics that really matter.

This month’s newsletter pulls together a set of practical reflections from the work I’ve been doing with founders recently — around building healthier sales pipelines, approaching fundraising conversations with more clarity, and understanding where real momentum actually comes from.

I’ve written about:
 – How different types of deals behave in a sales pipeline, and why recognising runners, repeaters, and strangers gives you far more control than simply chasing volume
 – How to make investor outreach more effective by grounding it in facts, traction, and clear intent
 – Why most founders’ networks are stronger than they realise — and how to surface opportunities that are already close by
 – Why early-stage startups grow faster when they lean into momentum rather than caution
 – And a personal lesson from a recent HYROX race that reinforced how progress often emerges from consistency, support, and resilience

If you’re building, scaling, or setting the tone for the year ahead, I hope this one leaves you clearer and more confident than when you started reading.

Introduction This newsletter is focused on the things that genuinely move startups forward at the start of a year: sales, momentum, decision-making, a

Open article: Momentum Over Comfort: What Actually Moves a Startup Forward by Ben Sheppard • 11 min read

Momentum Over Comfort: What Actually Moves a Startup Forward

If you’re building an early-stage startup, this will probably feel uncomfortable.

Early on, you don’t win by playing safe. You win by tearing the band-aid off, taking risks, and learning fast — even if that means failing multiple times in a single day.

What I see go wrong is founders hitting seed stage, or raising a decent round before revenue, and suddenly acting like there’s something to protect.

There isn’t.

You’ve got an idea, a rough product, and some runway. Treating those as fragile is how startups get stuck on the hamster wheel.

This short animation is built from my own experience — where this mindset worked, and where ignoring it caused real problems.

If you’re pre-revenue, just into revenue, or you’ve raised before proving the model, watch it properly.

Then ask yourself whether you’re managing risk — or just avoiding it.

Early-stage startups don’t need protection. They need momentum.

Early-stage founders often get stuck because they start behaving like they’re running a company that already exists.

If you’re pre-revenue, just into revenue, or you’ve raised without proving the model yet, this is how you should be thinking and operating.

Early

My stress levels don’t rise when things get tough.
They rise when I don’t have a plan. (and when I see my son with my wallet)

You know the pattern:
You get busy.
You put out fires.
You work day-to-day and call it “productive.”
 
But under the surface, something feels off.

Because without a plan, your brain goes into quiet survival mode.
And survival mode always catches up.

You stop seeing the big picture.
Execution drifts.
Momentum fades.

Suddenly you’re on the back foot — runway shrinking, customers frustrated, product slipping.

Here’s what took me years to understand:

A plan doesn’t remove uncertainty.
It removes chaos.

My own rhythm is simple: OKRs, weekly sprints, contingencies, and a clear structure.
It’s not glamorous — but it keeps the stress low because I know exactly how I’ll work through things when they go wrong.

Some people are naturally organised. Most aren’t.
And those who aren’t need structure the most — not as punishment, but as protection.

A plan gives you confidence.
Contingency gives you calm.
Structure gives you space to think.
When those are in place, I’m steady.

When they’re not, my stress tells me long before the business does.
If you’re feeling the wobble, start there.

Not with more tasks — but with a plan you can actually execute.

Most founders judge sales by size only.

I’ve learned to judge them by behaviour.

Some revenue stabilises your business. Some creates momentum. And some looks incredible while quietly increasing risk.

This carousel breaks down how I think about runners, repeaters, and strangers — and why misunderstanding the mix is one of the fastest ways to destabilise an otherwise healthy company.

Swipe through.

Understanding the Sales That Shape Your Business

This is Bugsy, wearing Harry’s favourite dinosaur slippers.

Now that I have your attention, I’ve just updated my coaching website.

If you’re a founder or operator navigating growth, complexity, or just needing a clear thinking partner, take a look.

www.bensheppard.xyz

Have a great weekend! 😉😊

No alternative text description for this image

Most bad decisions I see in growing businesses aren’t made recklessly.
They’re made under pressure.

A big opportunity appears. The clock is ticking. Saying yes feels bold. Saying no feels risky. And slowing down feels like you might miss your moment.

This is where founders get caught out — not because they don’t understand sales, but because they don’t have a simple way to think about what a deal will do to the business after the excitement fades.

I’ve put together a short animation that explains how I think about different types of sales, and why the smartest founders optimise for stability before scale.

If you’re facing a “this could change everything” opportunity right now, this one’s worth two minutes of your time.

Most founders get excited about the biggest deal in the pipeline.
I’ve learned to be cautious of it.

Not all sales behave the same. Some build stability. Some create momentum. And some look incredible in the moment but quietly introduce risk.

I’ve written about how I think about runners, repeaters, and strangers — and why the most exciting sale is often the one worth slowing down for.

See my full write up below

I often talk to founders and operators about sales pipelines, but what we usually miss is that not all sales are created equal. They feel the same whe

Open article: The Most Dangerous Sale in Your Pipeline by Ben Sheppard • 5 min read

Most companies don’t need a new strategy.
They need the same reality shared across the leadership team.

I worked with a 28-person company recently.
They’d just raised $30M — and still hit a stall.

Every leader had a different view of the problem.
Every team had a different plan.
And every week, the fog got thicker.

This is how companies quietly slide into trouble.
We aligned the truth, rebuilt the operating system, set the direction, and executed fast.

If your company is drifting, DM me

Grateful to read this from Tanya.

Building something on your own can be quietly hard — not always because of the work itself, but because there’s no one to sanity-check your thinking in real time.

I’m glad our conversation helped bring a bit of clarity when it was needed. Tanya is doing the work properly, and I appreciate the trust she placed in a simple, honest exchange.

Wishing you continued momentum.

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What are some of the ways you have overcome being frozen? 

Top Mentor (                                            5.0 / 5.0)

I work directly with founders and startup teams to raise capital, close customers, and make smarter decisions—faster. My practice blends deep operational experience with high-trust coaching and strategic advisory, tailored to the chaos and complexity of early-stage growth.

I’ve supported individuals, early-stage teams, SMEs, and global enterprises—helping them navigate fundraising, growth, and strategic inflection points. Clients span infrastructure, Web3, F&B, gaming, real estate, telco, and sustainability.

Support includes:
	•	1:1 coaching and advisory 
	•	Business planning, pivoting, and go-to-market strategies
	•	Fundraising guidance (equity, debt, token, grants), pitch refinement, investor readiness
	•	Sales strategy, partnerships and GTM execution
	•	Scaling hiring and team design
	•	Conflict resolution, leadership development, and high-trust decision support

I’ve built toolkits and frameworks to help founders navigate growth, raise capital, validate markets, and get investor-ready—used by accelerators, platforms, and top-ranked mentoring networks like MentorCruise.

I write about the highs, lows, and hard calls of startup life—from building companies to backing founders. Read more at bensheppardxyz.substack.com.

Strategic Advisor, Business Coach & Fractional Operator

Chief Product Officer (Fractional)

Silta AI is a vertical AI platform purpose-built for the infrastructure sector. It turns the mountains of documents, data, and complex processes that slow projects down into clear, actionable intelligence — across the entire lifecycle, from early feasibility to financing, construction, operations, and handback.

Unlike generic AI tools, Silta is designed for regulated, high-stakes environments. It applies sector-specific logic, verified frameworks, and precedent benchmarking to produce transparent, audit-ready outputs that decision-makers can trust. Every recommendation is linked to its source, with gaps flagged and compliance standards applied.

Governments, development banks, engineering firms, and investors use Silta to:
	•	Accelerate pre-feasibility and due-diligence reviews from months to days
	•	Streamline tender evaluations with explainable scoring and compliance checks
	•	Monitor construction and operations with real-time insights
	•	Manage project handback through automated gap analysis

Silta never trains on client data, offers white-label and on-premise deployments to meet sovereignty requirements, and integrates seamlessly with existing workflows. By enhancing — not replacing — human expertise, it extends the reach, speed, and rigour of infrastructure teams, unlocking billions in potential value and helping close the global infrastructure gap.

Co-Founder

Providing start-up mentoring to students participating in the GBSB Accelerator

Startup Mentor

Polakdot is a community-driven initiative advancing the adoption of real-world assets (RWA) within the Polkadot ecosystem. We build strategy, content, and partnerships to help the Polkadot community better understand and execute on RWA opportunities.
	•	Leading ecosystem-wide strategy for RWA narrative and use case development
	•	Supporting parachain teams in shaping RWA positioning and outreach
	•	Developing business development materials tailored to enterprises and institutions
	•	Facilitating cross-chain conversations and collaboration around supply chain, carbon, infrastructure, and DePIN use cases
	•	Acting as a bridge between Web3 builders and real-world operators

Business Development Consultant

I founded TX Technology Exploration Oy, the consulting arm of Tomorrow Explored (TX), and transformed it into a global B2B Web3 strategy and software company.

We worked across sectors—banking, NGOs, automotive, pharma, infrastructure, and ocean sustainability—helping enterprises explore the real-world applications of Web3 and tokenization.

Highlights:
	•	Closed major projects with UnionBank of the Philippines, Atos, World Wildlife Fund, and others
	•	Secured two major EU Horizon 2020 grants (Kraken: €450K, Atarca: €850K)
	•	Led high-performing consulting teams across Asia and Europe
	•	Designed token models and digital strategies for startups and global enterprises
	•	Launched a content-driven lead generation engine averaging 2+ inbound leads/week
	•	Created and hosted the TX Tomorrow Explored podcast, which hit the Apple Top 10 in Finland and featured leaders from both Web3 and TradFi sectors

Managing Director

At Streamr, I held multiple leadership roles during a critical period of growth following the company’s €32M raise. As Head of Streamr Labs, I led a small team of developers and designers focused on building innovative applications atop Streamr’s decentralised, tokenised data infrastructure. We explored practical use cases for real-time data exchange, helping shape the early application layer of the platform.

As Director of the Streamr Marketplace, I oversaw both the technical maintenance of the decentralised data marketplace and its commercial growth—onboarding new data providers and developing monetisation strategies to unlock value from real-time data flows.

In parallel, as Head of Partnerships, I led enterprise adoption efforts across sectors including mobility, infrastructure, smart cities, health, and supply chain—building successful relationships with Fortune 500s and multinationals such as OSISoft, HPE, Nokia, and DXC. I also served as a strategic advisor to the leadership team, designing the organisation’s operating model and supporting its transformation from a five-person startup into a 30+ person international company.

Head Of Partnerships, Marketplace Director, Head of Streamr Labs

Founded Bold Native Advisors to deliver technical and management consultancy for infrastructure projects in Southeast Asia, focused on major public-private partnership (PPP) schemes.

The company grew to 8 full-time employees and secured engagements with USAID, World Bank, Maybank, HSBC, MPIC, Rebel Group, and government entities in the Philippines and Malaysia.

Key achievements:
	•	Advised on high-profile PPP projects, including:
	•	Cebu Cordova Bridge ($600M USD project value)
	•	Cavite–Laguna Expressway ($656M USD project value)
	•	Supported transaction advisory and strategic planning for ministries and multilateral donors
	•	Reached $900K in annual turnover with 45% net margin in its strongest year

Due to political instability and shifts in ministerial direction in both the Philippines and Malaysia—our key markets—the business became unsustainable and was formally closed in 2019.

Founder & Chief Executive Officer

Co-founded a law and infrastructure advisory startup focused on public-private partnerships (PPPs) in Asia. Built the company from scratch to 16 professionals, including lawyers and technical consultants specializing in infrastructure development.

Key achievements:
	•	Secured high-profile clients including Bloomberg Philanthropies, Rockefeller Foundation, and the Asian Development Bank
	•	Led and won competitive bids for infrastructure advisory across Southeast Asia
	•	Designed the first-ever fishing port PPP for a Southeast Asian government
	•	Reached $1.2M in turnover in year one with above-industry profit margins
	•	Successfully exited the company just 18 months after launch

Founder, Chief Financial and Operations Officer

Held dual regional leadership roles across Europe and Southeast Asia, managing business development, delivery, and strategy for highway and bridge projects.

Key responsibilities & achievements:
	•	Oversaw a $5M regional P&L and directly managed ~35 staff across multiple countries
	•	Led winning bids for infrastructure consulting contracts worth up to $18M
	•	Managed project teams of up to 120 professionals across Asia and Europe
	•	Delivered major road and bridge projects for clients such as:
	•	UK Highways Agency
	•	Rijkswaterstaat (NL)
	•	World Bank
	•	Macquarie Bank
	•	Asian Development Bank

In the final year, was tasked by CH2M with managing the wind-down and strategic closure of the highway and bridge business unit in Southeast Asia.

Regional Director for South East Asia Highways and Bridges Market / European Market Manager

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

Founder, Entrepreneur, Growth

Since I started my company, I’ve met many people, some disappear quickly, some help without promising anything, and some truly give their time, support, and conversation when it’s needed most.
Ben Sheppard is one of those people. He listened, responded, and shared truly useful, actionable insights.
For a solopreneur, even a short, genuine conversation with another human can mean a lot.
🙏 Thank you to everyone who has extended a helping hand. I truly appreciate you.

I’ve seen this pattern more times than I’d like.

A big deal lands.
It’s exciting. The fee is meaningful. It feels like the business has just levelled up.

To deliver it, the team stretches. New people come in. Focus shifts. The core work gets less attention — but it’s fine, because this deal is worth it.

Until it ends.

And suddenly the cost base is higher, the pipeline hasn’t caught up, and the revenue that used to quietly hold the business together isn’t enough anymore.

The problem isn’t the deal itself.
The problem is misunderstanding what kind of sale it really was.

I’m writing about this tomorrow.

I couldn't agree more with Blaine. Also, if you have a side hussle you're less reliant on the finances of your startup, which means you can go longer without needing to raise.

High performers almost always have a side project going on – it sharpens how they think.

I’ve seen this pattern over and over again. And I’ve heard the same thing from mentors I deeply respect.

One of them, a multi-exit founder, once told me that some of the best co-founders and operators he’s ever worked with were always building something on the side: a small business, a product, a passion project. 

At first, it sounds like a red flag:
“Isn’t that a distraction?”

But in practice, it usually isn’t.

High performers just have more horsepower. They’re channeling excess energy. 

And working on something in your free time actually makes you better at your main role.

You stop thinking inside the vacuum of one company.
You get reps solving problems with different constraints.
You’re forced to think creatively instead of defaulting to the same patterns.

It’s definitely not for everyone.

But in my experience, it helps people think differently.

Really grateful to Sarah Taylor  for taking the time to leave this review.

Working inside Envoqe is a genuinely enjoyable experience. It’s an opportunity to go deep into spatial intelligence, cognitive performance, and the transitions people move through in work and sport—and how those transitions directly influence performance.

What I particularly value is the thinking behind how these insights are applied in practice: how decision-making, confidence, and execution can be optimised to create consistently high-performing, winning environments. It’s been a privilege to contribute while also learning alongside Sarah as Envoqe continues to evolve.

Looking forward to continuing the work together.

Executive Coaching, Business Consulting, Project Management, Change Management, Leadership Development, Negotiation, IT Consulting, Product Marketing, Marketing Strategy, and Pricing Strategy

Building a company can be an isolating and overwhelming process, and having the right people beside you makes all the difference. Ben has been an exceptional mentor and, as a fractional CPO, brings a wealth of experience and clarity to complex decisions. He is exceptionally generous with his time, helping build confidence in uncertain moments. Ben has genuinely shaped how I approach building and positioning my businesses. I’m incredibly grateful for his support.

Sarah Taylor reviewed Ben’s Business Consulting services

Amandine is a very hard worker, I highly recommend her.

Startup Operator 0-​>1| Former Co-founder WildMeta AI | 15y leading cross-functional projects | 🏆 Winner of OpenAI, Arm & AMD developer contests

New year, new introduction 👋

My name is Amandine and I've spent 15 years working with fast growing B2B tech startups across ops, product, growth, and marketing.

Some highlights:
- Former co-founder of AI startup WildMeta (RL x gaming).
- 3x winner of ML developer contests including OpenAI Open Model Hackathon 2025 and AMD Pervasive AI 2024.
- Based in London, UK with experience working within international teams.

Now I'm looking for my next role. I'm drawn to infrastructure, compute, and teams tackling hard problems where technical depth makes the difference.

If you're building something ambitious or know someone who is, let's connect!

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