Iwo Szapar

Hybrid Work Expert

🚀 Remote-First Activist | Top 50 Remote Influencer | Since 2017, shaping the future of remote-first world

Aloha, I'm Iwo Szapar! Over the years, I've helped transform how over 3,000 companies approach work, leading to more efficient and enjoyable professional lives. 🌍

Key Achievements:

▪️Co-created the AI Maturity Index with Harvard researchers, democratizing access to enterprise-grade AI readiness insights
▪️Advised Ministry of Communications and Technology of Saudi Arabia on AI up-skilling for startups
▪️Launched world's first certification program for remote workers: Remote-how Academy, back in 2018.
▪️Established strategic partnerships with 150 companies, including Asana, Deel, Remote, and Safetywing.
▪️Created an expert community of 250+ consultants from companies such as GitLab, Netflix, and Hubspot.
▪️Co-organized 3 editions of Remote Future Summit, reaching over 11,000 attendees and featuring 140 speakers.

Born in Gdansk, Poland, I've embraced the 'slowmad' lifestyle, living in various countries while working remotely. This journey has enriched my perspective and fueled my passion for innovation. When I'm not working, you can find me reading history books, following international affairs, or indulging in my hobbies as a dog lover, amateur surfer, and DJ.

Connect with me to explore how you/your company can work smarter! 🚀

🚀Remote Work Advocate & Co-founder

Remote-how helps companies make remote & hybrid work, work. Since 2017. 

🤓 Remote-how Marketplace - the world’s leading remote & hybrid work experts marketplace. Work on your consulting and advisory projects with 200+ pre-vetted practitioners from top distributed companies. 

🚀 Remote-how Campus - a community where leaders of hybrid teams come to connect, learn and grow together with access to live leadership development programs, mentoring services, and more.

$50k revenue in three months from a side-project. Two other products in the making, while working my half-time job. 

No team. 
No VC. 
No startup story. 

A small, profitable product.

Just me + dozens of AI Agents, and an obsession of going AI-first with 99% of work tasks I do.

IE University's podcast asked what advice I'd give entrepreneurs. My answer surprised them. (I guess...😅 )

Forget the unicorn. 

Build small. 
Build profitable. 
Build alone if you have to.

Skip the unicorn obsession. 

The founders winning right now are the ones running lean, staying profitable, and using AI as their operating layer instead of a headline.

Now advantage goes to whoever moves before the playbook is written - right now, that's the lean operator, not the firm with 500 analysts."

Keep in mind that we're at maybe <5% AI adoption globally. 

Still the first inning. 

The window to figure this out before everyone else does is narrow.

Is the lean founder model genuinely better - or does it only work for certain product types?

Sooo... coming back to the interview: Ainhoa asked great questions, and our conversation went places I didn't plan for.

Enjoy tull episode in the video - link in comments.

Gracias Ainhoa for a super energising chat and Mercedes for the invite ❤️ 

Sending good vibes to my IE / South Summit friends and hope to see you in a few weeks in 🇧🇷 Victoria Juan Christopher Joe Francisco Geoffroy Nacho Liz João Camila Mateo Juan Andrea Emma María Maria Gabriela Fernanda

You read posts about AI every day. That does not put you in the top tier.

0.04% of humans use AI daily to ship real work. 

0.3% pay for any AI tool. 

The rest are observers.

Reading about AI, sharing posts about AI, attending AI workshops: none of that moves you up the distribution. 

Building something does. 

Running a model against your actual work does. 

Getting Claude Code to do a real task in your real environment does.

I deployed Second Brains for 85 people. 

The ones who moved tiers fastest did one thing differently: they stopped consuming AI content and started running experiments inside their own work.

The AI revolution people keep announcing has not happened. 

For 99.96% of people, it has not started.

You already know what to build. 

The gap is not ideas. 

Where do you stand with AI adoption?

Start here: https://lnkd.in/dgqpKJyd

AI Adoption Tiers among knowledge workers 2026 

I cancelled my ChatGPT subscription last year. Now OpenAI sees a mass exodus of users. Why? 

It’s following the deal with the Pentagon over AI military use, where Anthropic rejected the deal due to its firm position on AI ethics. 

The CEO Dario Amodei refused to accept the deal for two reasons: 
- the use of AI for mass surveillance of American citizens
- managing autonomous weapons.

Is this a temporary problem for OpenAI or a part of a bigger trend where they might loose the pole position in the AI labs competiton? 

PS. Have you cancelled your ChatGPT subscription - what was the reason? Have you joined the Claude Code family for good?

Thank you IE University for having me ❤️ Muchas gracias! 🫡

The latest episode of Venture Ahead explores the future of work with Iwo Szapar, an entrepreneur, writer and speaker and the founder of the AI Maturity Index.

From the rise of remote work to a world shaped by automation, augmentation and distinctly human skills, this conversation, recorded during South Summit Madrid, dives into the profound shifts redefining how we work and how we live. As AI agents move from prediction to reality, the question is no longer whether change is coming, but how we adapt to it.

For founders, leaders and professionals navigating this transformation, this episode offers a sharp look at what’s just beginning.

Watch now and #VentureAhead: https://lnkd.in/edN3fx8V

Ainhoa Valencia | Victoria Pérez Jiménez | Juan José Güemes | IE Entrepreneurship & Innovation Center | IE University Lifelong Learning

I built a tool that grades AI Second Brain setups. It gave my own setup a 76% 😅

Everyone assumes the person who builds the grading tool at least passes their own test.

Overall: 80% - Grade A. 

But Setup Quality scored 76%. 

That's a B.

397 out of 499 points across 140 automated checks.

Here's where it got embarrassing:

1. AI Fluency: 93%. Five checks scored perfect. Reference Integrity: 60%. My files point to things that don't exist. Embarrassing when you're the one who wrote the scoring logic. 

2. Setup Quality: 76%. Model Configuration scored 0%. Sandbox scored 13%. I literally skipped the config I tell other people to set up. Progressive Disclosure: 98%. 

3. Self-Correction and Compound Learning: both under 60%. The system I built knows I'm not using half of what it checks for.

The tool placed me at COMPOUNDING - fourth of five levels. 

Not yet Production-Grade. 

Which means there's a ceiling I haven't hit yet.

Three fixes would add 14 points:
- Auto Memory (+5)
- Quality Tracking (+5)
- Growth Log (+4)

Fifteen minutes of work I keep putting off.

The tool is Open Sourced - it's free. 

If you want to be publicly humiliated by your own setup, install it in one line:

claude mcp add second-brain-health -- npx second-brain-health-check

Read more: https://lnkd.in/dqnjpsrd

Full breakdown in the carousel.

What's the one part of your setup you know is broken but keep ignoring? 

Mine was Model Configuration. Scored 0%.

Second Brain Health Check Iwo Szapar 2026

AI tools made my clients productive. Then they asked me to remove every single one.

Not because the tools were bad. 

Because every tool came with the same trade-off: someone else owned the intelligence.

Notion AI? Your data on their servers. 

ChatGPT? Zero memory between sessions. 

CRM automations? Break the moment your workflow changes.

After building 81 Second Brains across 12 industries, the pattern is always the same. 

People start with tools. 
Then they want a system. 
Then they want to own it.

What they actually want is a fourth category that nobody talks about.

A system built to their exact workflow. 

Running on their own infrastructure. 

Vendor-independent. Claude today, GPT tomorrow, Gemini next month. 

You own it. Completely.

The discipline behind this is context engineering: managing what the AI knows, when it knows it, and how that knowledge compounds across sessions.

The industry default is renting intelligence from a vendor. More and more people want to own it instead.

Does that gap feel real to you?

I'm packaging v2.0 in the next 7 days.

Comment below what an ideal Second Brain should do for you 👇

AI is like a box of chocolates. You never know what you're gonna get, but it will absolutely be confident it gave you exactly what you wanted.

Founder & CPO at Upflex I Investor I Strategic Advisor I Coach & Mentor

I’m a builder at heart of products, companies, and communities.
With 20+ years of experience across North America and Asia, I’ve worked at the intersection of innovation and impact, helping startups transform bold ideas into real-world solutions. From the future of work to healthcare, e-commerce to fashion, I’ve led teams from zero to launch and scaled to global growth.

One of my early career highlights was joining Embedded Wireless as the first employee. What began as a small office in Kuala Lumpur quickly evolved into a global operation. I helped build and scale cross-functional teams across India, Ireland, Malaysia, Bangladesh, and the U.S., bringing together a diverse and talented group of engineers and leaders. That experience shaped how I think about scale, collaboration, and the unmatched strength of global talent diversity.

Today, I’m the Co-Founder and Chief Product Officer at Upflex, a platform that reshapes workspace access for distributed teams. I’m also a Partner at Sero Partners, a New York-based advisory and investment firm that helps growth-stage companies expand and access capital through a trusted network of VCs, family offices, and operators.

As an angel investor, I actively support early-stage startups, especially those led by women and focused on AI, the future of work, and global impact. Diverse teams build better products and a better future.

Patents + Collaborations
• WO 2014145779 A3 – Personal Health Server & Ecosystem
• US 20050114366 A1 – Personalized Online Services & Ads in Public Spaces
• WO 2004068296 A3 – Online Commerce
• WO 2000041543 A2 – Single-point to Multipoint Data Communication

Always up for meaningful conversations — especially at the edge of what’s next.

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