From Rejection to Resilience: Acumen Law’s Penina Shepherd on Bold Business, Feedback & Fearless Leadership

When you think of launching a law firm, you probably don’t picture doing it in the middle of a global recession, while raising three children, battling cancer, and starting from scratch.

But that’s exactly how Penina Shepherd started Acumen Law, and in this blog she tells us exactly how she did it.

A proud Brighton-based entrepreneur (and one of our brilliant VIP Connected100 members), Penina joined us for a candid, funny, and powerful conversation on founding a people-first law firm, listening to your gut over feedback, and why fear can be the most persuasive voice in the room.

The content from this blog is taken from the Connected Brighton Podcast - Episode 48 - The one with Penina Shepherd

Launching a Business in the “Worst” Possible Moment

Penina didn’t have the perfect business plan, a financial safety net, or an ideal window of opportunity. What she did have was a strong sense of purpose — and a refusal to let fear dictate her future.

“I had no clients, no money, a newborn baby, two other kids under ten, and I’d just been diagnosed with aggressive cancer… and I launched Acumen Law in a recession.”

So why do it?

Because, as Penina says, fear is incredibly convincing.

“Fear has the best lawyers. The arguments it gives you are solid. But nearly everything we want in life is on the other side of fear.”

Why Feedback Isn’t Always Useful

One of the boldest takeaways from this episode is Penina’s view on feedback — especially for entrepreneurs.

“The people giving you feedback aren’t doing what you’re doing. Their fears, their projections — they’re not yours. And that’s why feedback can be useless.”

She explained that even the most well-meaning friends, mentors, and clients aren’t inside your vision. Their advice often reflects their own limitations — not your potential.

Her advice? Listen selectively. Trust yourself fully.

The Three Essentials for Growing a Bold Business

When asked what helped Acumen thrive, Penina didn’t cite strategy or spreadsheets. Instead, she gave us three human, heartfelt foundations:

1. Have a story to tellAs Penina puts it, “People connect with people.” She believes being open about her journey has helped build genuine trust and community.

2. Lead with passion“When you’re excited, people want to be part of what you’re doing,” she says. Her energy and love for law — and people — has always been contagious.

3. Stand outAcumen Law did things differently from day one — ditching hourly billing, giving out mobile numbers, and injecting colour, creativity and personality into a traditionally formal industry. As Penina says: “You’ve got to be the purple cow.”

How Acumen Law Flips the Corporate Script

At Acumen, culture comes before hierarchy.

“We don’t do corporate announcements. Everyone sits around the table, whether you’re a student placement or a senior lawyer. Everyone’s part of the conversation.”

That transparency and trust has shaped a team that sticks around. Two of her longest-serving colleagues, Dan Jones and Alvin, started as paralegals and are now equity partners.

“People want to grow, but they also want to belong. We create space for both.”

Making Law Approachable (and Actually Useful)

Outside the boardroom, Penina is also known as Little Miss Legal - her TikTok alias, where she breaks down legal myths and offers one-minute wisdom to help people before they hit crisis point.

“You’re not trying to teach everything in 60 seconds. But you are planting a seed, and showing people you’re here to help.”

Looking Ahead: Acumen Business Convention (With a Twist)

As Acumen Law heads into its 18th year, Penina hints at what’s next: an evolution of the well-loved Acumen Business Convention.

“We’re calling it ‘Acumen After Dark’… it’s going to be fun, a little cheeky, and totally different. But still all about business, community and connection.”

We can’t wait.

Final Thoughts from Penina

Penina’s story is a reminder that courage doesn’t mean having no fear — it means moving forward anyway.

From launching a firm against the odds to rewriting what leadership looks like in law, she’s proof that your story, your values, and your energy are your strategy.

“Don’t wait for it to make sense. If you feel called to something, do it messy. Do it afraid. Just start.”

The content from this blog is taken from the Connected Brighton Podcast - Episode 48 - The one with Penina Shepherd