💡 A Hollywood Portfolio Career Face-off

When I think about a public portfolio careers done well, one name instantly comes to mind: Ryan Reynolds. Not only is Ryan an A-list actor, but he's also a co-owner of Mint Mobile, Aviation Gin, and a Welsh football club. His career is a brilliant example of how to leverage early career strengths to build a diversified career portfolio over time.

Then there’s his wife, Blake Lively. 

Don’t get me wrong — Blake’s transition from her breakout role on Gossip Girl to big-screen actor was impressive. But when she tried to expand into lifestyle ventures, the results were less stellar.

Why such different outcomes? Let’s unpack this together — because I believe the difference goes beyond Hollywood drama.

Turning Personality into Profit

Ryan’s approach highlights a few principles that I believe make for a solid portfolio career and personal brand.

Here they are:

• Authenticity: One of the reasons why we continue to love Ryan is because the business investments he makes feel like an extension of his personality. His quirky humor is embedded in Aviation Gin’s ads, Mint Mobile’s campaigns as well as his involvement in rebuilding Wrexham FC.

• Early Strategic Focus: Ryan’s eyes weren’t bigger than his stomach when he started expanding beyond Hollywood. Instead of dabbling in 20 ventures at once, Ryan prioritized a handful of businesses where he could make an immediate impact. In fact, he was present and visible in each, which amplified the credibility of said investments and helped his fanbase make better sense of his professional extension beyond his acting career. IMHO he effectively created the necessary cohesive career narrative that reads something like this: actor turned savvy business owner.

• Play to Your Strengths: Ryan’s humor, storytelling skills, and relatability are his superpowers. By leveraging these, he helped each portfolio brand’s marketing team connect with their target audience more quickly and effectively. The bonus? It also reduced ad spend—a triple win!

• Outsource What Your Not Good at: Ryan’s efforts focused on his zone of genius - storytelling and charm. And he outsourced the rest of the business operations to a select group of top-tier operating partners. This approach allowed him to scale his impact across more brands once he mastered managing multiple businesses simultaneously.

🔍 Case Study: What Happened at Preserve

Blake’s approach, on the other hand, with the launch of her lifestyle brand Preserve, provides a cautionary tale of the negative business outcomes that can arise when a portfolio brand strategy isn’t carefully thought through.

Here’s my breakdown of why the launch ultimately failed:

• Lack of Cohesive Vision: Preserve launched without a clear identity. Was it a blog? An e-commerce platform? A lifestyle guide? The site tried to be everything and, in turn, ended up being nothing. Without focus, it couldn’t connect with any audience. No bueno.

• Lack of Authority or Credibility: Blake aspired to emulate Martha Stewart with the creation of Preserve. However, this leap introduced a version of Blake that the public wasn’t familiar with, and there was no credibility-building period to bridge that gap. As a result, her public brand felt disconnected from her established identity. Preserve seemed to come out of nowhere, attempting to replicate Martha Stewart’s success without the authority or transitional steps needed to make the shift feel authentic. What could have worked? Taking time to build credibility as this new persona or leaning into what she was already trusted for bringing to market—a curated, high-end NYC-inspired lifestyle or clothing brand. Something exclusive and insider, like artisanal candles—paired with sleek city essentials. Preserve needed to feel authentically “Blake,” not like a borrowed persona.

• Rushing to Market: Lively's own words say it all. In her shutdown letter, she candidly admitted Preserve was "an idea greater than its current representation"—a poetic way of saying, "We were not ready." The business was pushed to market just six months after its inception, spurred by the promise of a front-page cover on Vogue. It was simply too much flash, too soon.

• Pricing: I’m curious what the thought process was for pricing artisanal products over $200 a piece. This misstep in the marketing mix speaks for itself.

• Operational Overreach: Lively attempted to compete with established lifestyle giants like Goop without the necessary operational infrastructure or industry expertise. It was akin to bringing a butter knife to a gunfight—well-intentioned, but ultimately ineffective.

• Lack of a Brain Trust: Building a portfolio career or your own business requires surrounding yourself with people who will challenge your “eyes bigger than your stomach” ideas. This trusted circle of advisors—a brain trust, if you will—can help identify strategic missteps before they happen. In Blake’s case, her stardom may have created an environment where those around her were hesitant to speak up. I’m rewriting history here, but I believe that Blake having a brain trust could have been the difference between the rushed product launch of Preserve versus a more thoughtful, extended one that was better aligned with her grand vision.

• Overextension: Last but not least, I believe a significant challenge to Lively’s success with Preserve was attempting to build a lifestyle brand while simultaneously reviving her acting career. After a four-year hiatus, she returned to star in four films in a single year. Where was the time to focus on the details of Preserve, I wonder?

Before wrapping up this analysis of Preserve, I do want to acknowledge something important: launching a new venture—especially one in the relentless public eye—is no small feat. It’s easy to look back now on Blake’s decisions wrt Preserve and critique them with the clarity of hindsight, but my goal here isn’t to nitpick. It’s to highlight what the timeline and executional challenges in this particular example can teach us as portfolio careerists about the importance of thoughtfulness and attention to detail as we layer in new revenue streams.

In sum, building something meaningful and great takes time. There is no rushing past the details and mechanics, really.

Key Takeaways

In sum, the success of your portfolio career largely depends on having a clear strategy for layering in income streams and product lines over time.

Why? Because YOU ultimately ARE the product. And once you erode trust, it’s hard to gain that back from your audience.

Remember to:

• Play to your Strengths: Know your superpowers and integrate them into every venture you pursue.

• Take your Time: Test your ideas fist and refine them before a full blown commercial launch.

• Be Selective: You simply can't “do it all” all at once. Focus on a few aligned projects where you know you can shine, especially at the beginning.

• Build a Brain Trust: No one succeeds alone. If you can, hire. If you cannot, surround yourself with a group of strategic advisors who you believe will complement your skill set. Ideally these are also individuals that will call you out on your bad, eyes-bigger-than-your-stomach ideas!

🎬 Your Turn Now!

Grab a notebook and reflect on your own portfolio career:

• Which of your current projects feel like a natural extension of you?

• Where do you feel overextended or unclear about your goals?

• What strengths should you double down on to bring cohesion to your portfolio?

• Which of your projects or experiments needs more thought and time?

Want help mapping it all out? I have 1:1 coaching spots open next month — go ahead and click here to book!

📚 Free Vision Boarding Workshop

Kickstart 2025 with an intention

I haven’t done a virtual workshop in awhile so I am excited to announce that on Sunday January 5th at 5 PM Pacific / 8 PM Eastern, I’ll be hosting a free virtual Vision Boarding Workshop.

I’ll guide us through a visioning exercise to craft our Phrase of the Year—a powerful tool that is meant to set our focus on the growth and abundance we each want to cultivate in the New Year.

So bring your favorite craft supplies and your imagination ✏️🎨

What to expect:
🌟 A few reflective prompts from moi to get our creative juices flowing
🌟 A supportive space to share and process your vision
🌟 Connection with a welcoming community of fellow portfolio careerists

Ready to set some intention anchors to stay motivated all year long?

I’m keeping it cozy so RSVP now to snag a spot here! 🎉