Hi there,

Back home in Mexico City from our honeymoon and feeling refreshed! 😎 

This week’s edition is going to be a quick one covering what you can expect from me and the team at Portfolio Path for the rest of 2025 and beyond.

Let’s dive in!

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Our alums include over 100 mid-career/senior professionals from Google, Apple, Stripe, Tik Tok, and fast-growing startups.

After this cohort ends, the Launchpad will only be accessible as a self-paced course within our community.

Here's what you need to know:

• Waitlist Enrollment opens September 3, 2025

• Only 10 Spots Are Available

• Cohort kicks off on September 17

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🚁 A new vantage point

Last week, I felt terrified I was going to fall out of helicopter over the eroded volcano.

We took an open-door helicopter ride in Kauai, and I was surprised by just how beautiful the lush landscape looked from above vs from the ground.

The waterfall-laden mountains were like a scene out of Moana. Seriously.

For the past 6 months, I’ve been heads down - in the weeds - of building Portfolio Path.

On my honeymoon, I got to see things from a different vantage point, connect the dots, and envision what work looks like for me in 2025 and beyond.

Through my reflections, I realized what’s most important.

When I launched Portfolio Path in February, I didn’t set out to just teach consulting tactics.

Our mission has always been to empower intentional high-performers to live on their own terms.

Yet after talking to hundreds of our readers/members (mainly tech workers), a few patterns emerged:

• Professionals feel heightened fear/anxiety around economic volatility and disappearing traditional job security

• People recognize AI helps future-proof their careers, but don’t know what actually moves the needle

• Portfolio careers are highly desired, but people don’t want to do it alone nor get left behind

The biggest barrier to taking an unconventional career path doesn’t seem to be possessing enough role-related expertise but rather the fear of navigating this shift alone/getting left behind during a tough economy.

That’s why Portfolio Path is evolving to meet your needs.

Over the next few months, we’re doubling down on content and programs that help you adapt to this rapidly changing work landscape - and build sustainable portfolio careers in the 2020’s.

Below I share three key updates you can expect from the newsletter and programs help you start, grow, and thrive on your portfolio careers.

🗺️ Recapping where we’ve been

I’m proud of the milestones we’ve crossed in the past few months:

• Launched a brand-new community with over 40 members including ex-FAANG professionals, fractional CTO/CFO/COOs, agency owners, and PT tech consultants

• Completely revamped our Launchpad product, delivered 2 strong cohorts (9/10 avg rating)

• Launched the Blueprint, generating our first digital product revenue

• Helped dozens of professionals launch portfolio careers via our programs

Not to mention more mundane things like fully migrating off the Kajabi platform (ugh).

With that said, it hasn’t always been smooth sailing.

I experienced my fair share of entrepreneurial anxiety/self-doubt, witnessed the gradual erosion of social media, and had to make hard decisions about market direction.

Despite these challenges, Portfolio Path is alive and stronger for it.

Now here’s what you can expect from us going forward:

🔑 What you can expect from us

We’ll be doubling down on Portfolio Path becoming the leading community for portfolio careerists to experiment, learn, and grow together.

Our focus is serving mid-career professionals - especially those in the tech industry and/or possessing a startup/entrepreneurial mindset.

I’ve learned that in the AI era, it won’t be enough to possess skills. Judgement and relationships will play a huge role in differentiating yourself in the talent market.

That’s why I strongly believe communities will be essential for those seeking career autonomy.

Communities are a unique opportunity to build peer, mentor, and partner relationships that can help you take control of your portfolio path.

Personally, I’ve received heaps of value from being a part of multiple professional communities - from growth groups in SF in my early career to entrepreneur/creator circles today.

In the Portfolio Path community, we’ll accept a limited intake of new members every month to ensure a high-quality experience. (You can apply here.)

Meanwhile, I'm spending more time working on AI projects.

I enjoy nerding out on emerging tech, but that’s just one reason why.

As I’ve written previously, I view high-leverage AI adoption as a key trend enabling the rise of 10x workers and portfolio careers.

I’ve already started seeing small teams become insanely productive, underscoring the potential emergence of new business/employment models. This is exciting to me.

For example, some of our community members are already heavily using AI to run their agency/service businesses. Using the tech, they can scale their output and deliver a more compelling client experience without hiring more staff like 5 years ago. Pretty cool.

My goal is to stay 6-12 months ahead of the curve of what’s practically possible in AI to help business owners get more leverage and take control of their time.

Along the way, I’ll share what I learn as much as possible with you - so that you can apply it to your own portfolio career or business.

Here’s what this means for you:

1. More signal, less noise. Instead of weekly updates, you’ll receive bi-weekly high-quality deep dives starting September 14th.

2. Final Launchpad LIVE cohort starting in September. Afterwards, it’ll only be accessible as a self-paced course in our community membership. If you've been thinking about launching a consulting business, this is your last chance to join our popular 8-week program.

3. Practical AI content. I'll write about specific AI business workflows and insights helping our members leverage their output by 50%, 2x, or even 4x.

🙏 That’s a wrap

Keeping this edition short and sweet. For everyone reading over these past few months, thank you for supporting Portfolio Path.

I owe a lot of our recent successes to readers/members like you, and can’t wait to continue serving you over the coming months and years.

P.S. What do you think of this new direction? Reply and let me know your thoughts!

💎 Last Week’s Gems

🪴 How to Build a Career That Thrives Alongside AI (Ines Lee - our alum!)

🤑 2025 State of the American Investor (Fidelity)

🧑‍💻 These AI-Skilled 20-Somethings Are Making Hundreds of Thousands a Year (WSJ)

➕ What are you optimizing for (Jack Raines)

🤩 Community Spotlight

🇸🇬 Michael hosted our first-ever in-person Singapore meetup!

🇬🇧 Marilyn is launching her first event at the Royal Society of Arts in London on 8 September: When Everything Changes at Once: Navigating AI + Career Disruption

🤓 Deassy recently onboarded new global team members for her product research firm.

Join the waitlist for our invite-only community and we’ll notify you when our September intake begins: