Bold Business Podcast

Stop out-hustling yesterday. Rigid roadmaps and endless checklists can keep your team busy on priorities the market has already left behind, and that's how burnout and operational drag take hold. The linear business growth trap is seductive because it feels productive, but it leaves you executing without business instinct. In this episode of the BOLD Business Podcast, Jess Dewell , Strategic Growt...

It's not a strategy problem. It's a comfort problem. Change feels welcome until it asks you to move into new territory, and then it can feel daunting, even when you've hired outside experts. Sometimes the stress and frustration around AI disruption, rising costs, and burnout grow big enough that change has to happen. Other times, the real issue is business resistance rooted in a future that isn't...

Growth is uncomfortable. Amy Anderson didn't plan to become an entrepreneur—a divorce and two young children forced the decision. What she's built since then, scaling from two people to 20 while running a fully dispersed team, offers real lessons in performing under pressure while staying true to your values.  In this episode, Jess Dewell talks with Amy Anderson , Co-Founder at Wild Coffee Marketi...

Your commitment to yourself determines everything else. Most leaders show up for their clients and team with unwavering dedication—yet struggle to honor the same promises they make to themselves. This gap is where potential goes to die. In this episode, Jess Dewell talks with Paul D. Casey , Coach and Author at Growing Forward Services , about why reflection, intentional decision-making, and perso...

Your growth strategy is already outdated. That's not a failure — it's a reality. In this episode, Jess Dewell talks with John Sansoucie , CEO at CogNet , about what it takes to scale from startup to enterprise while staying aligned with a market that never stops changing. CogNet grew 600x. Along the way, John learned that the most dangerous assumption leaders make is thinking their strategy is sta...

Intentionally investing in your own and your team's personal brand is the single most powerful advantage to scale your company—especially during the high pressure and rapid change you face today. In this episode, Jess Dewell talks with Anne Candido and April Martin i, Co-Founders at ForthRight People , about how self-awareness fuels BOLD moves in business and how aligning behaviors with your trues...

Find out if your brand is built to last — or just chasing the next trend. Thinking with a longer horizon (even 20 years!) is the edge your business needs to withstand today's constant change. In this episode, Jess Dewell talks with Bob Rogers , Founder at BRC Imagination Arts and Author of "Deep Story A Masterclass in Experiential Story Making," about how practicing ruthless focus around one objec...

In the age of AI, the traditional concept of hustle and brute force work is becoming outdated. Jess Dewell talks with Duncan Brand , Author of Mind the Gap and Effectiveness Advisor, about why it is BOLD to build systems-led execution and make themselves obsolete in day-to-day operations.   Uncover the secret weapon top leaders use to break out of overwhelm, refocus priorities, and drive lasting a...

You hired the best team, invested in the latest tools, and built what looks like a scalable operation. And nothing changed. Not because your people aren't talented — but because you're still playing the wrong role. You're still doing work that someone else could do better. The future of scaling isn't about building bigger teams or buying the next tool. I''s about knowing yourself — truly knowing w...

Align your actions with desired business outcomes, even when it requires challenging current habits. In this episode, Jess Dewell talks with Chris McShanag , CEO and Founder at Virtual Teammate , about boldly confronting distraction debt and using growth levers to scale. He shares proven strategies that help owners and executives ditch low-value work, redeploy talent, and fuel business growth — wh...

Prepare for the worst, hope for the best. Scenario planning isn't just for financials. Whether markets drop or your business faces adversity, having thought about the worst-case lets you operate with confidence. In this episode, Jess Dewell talks with Jack Oujo , Founder at Oujo Wealth Strategies , about why it is BOLD to embrace the concept of less is more — especially in today's fast-changing wo...

Stepping up is essential for you, your team, your customers, and your service to create real impact. In this episode, Jess Dewell talks with Heather Gibson , Owner at Big Hearted Breeders , about how recognizing self-doubt is necessary for self-acceptance in the process of facing industry disruption. She shares that she is BOLD in order to meet the self-doubt that arises by remembering her purpose...

You just invested in the latest feedback tool, the best collaboration platform, the smartest productivity software. And nothing changed. Not because the tools are bad — but because you're still measuring the wrong things. You're still rewarding the visible. You're still missing the people who quietly hold your organization together. The future of work isn't about better tools. It's about measuring...

Your team is tired. Not because they're working hard — it's because nothing finishes. Projects linger. Code stays half-baked. Strategy documents gather dust. Trust frays. And the worst part? Nobody can name what's actually wrong. Because the real problem isn't the work itself. It's that half of it never ships. It just sits there, unfinished, invisible, draining energy from everyone who touches it....

Growth plateaus aren't inevitable — they're a signal. In this episode, Jess Dewell , Growth Strategist at Red Direction and host of the BOLD Business Podcast, reveals why even high-performing CEOs and founders hit a ceiling and how to break through it. The cycle of hustle is real, but scaling with intention requires more than speed — it demands strategy, self-awareness, and the courage to evolve....

The resistance your team is showing isn't about your direction. It's about being left out of the story. You have the vision. You have the answers. You know exactly where this needs to go. And that's precisely where you're losing them. Because a vision that lives only in your head isn't a company vision. It's a founder's private project. And teams don't sign up to be passengers in someone else's st...

You started your company because you were exactly what it needed. Then your company grew, and suddenly you became the problem. No one tells founders this part of the story — not in the highlight reels, not in the fundraising pitch decks, not until you're standing alone at 2 a.m. wondering if you're the one holding the business back. Scaling isn't just an operational challenge. It's a personal reck...

Are you your own biggest roadblock to success? In this episode, Jess Dewell (Managing Partner and Growth Strategist at Red Direction ) , Christy Maxfield (President and CEO at Purpose First Advisors ), and Dean Barta (Founder and CEO at Barta Business Group , have a candid conversation about what growth really looks like — and what it costs.   Growth isn't just about revenue. It means building inf...

Here's what kills growth quietly: not bad strategy or tired teams, but leaders who stop showing up with intention. When you're busy, when uncertainty rises, when the pressure mounts — that's exactly when trust starts to leak. And by the time you notice, it's already become your biggest liability. Trust isn't an intangible value or a soft skill. It's measurable, concrete operational infrastructure....

What if your routines are quietly stifling your company's growth? In this episode of the BOLD Business Podcast, host Jess Dewell sits down with Dr. Jennifer Berry , CEO of SmartLab , to explore a rebellious mindset shift that disrupts burnout and drives fresh thinking in today's fast-changing business landscape.   Dr. Berry challenges the "go it alone" approach to leadership, making the case that...

Most companies don't lose ground because their product weakens or their team stops working. They lose ground because the message drifted - gradually, quietly - while everyone was busy chasing the next platform update. A clear message isn't a marketing asset. It's operational infrastructure. And when algorithm shifts, shrinking social ROI, and an AI-saturated ad landscape all arrive at the same tim...

Growing companies often sacrifice the foundation while chasing the finish line. Culture gets built later. HR systems get installed when problems surface. Employee protections feel like a luxury for bigger budgets. And somewhere in the scaling sprint, leaders realize they've created the perfect conditions for workplace disputes, legal exposure, and the very chaos they were trying to outrun.   But h...

If you picture your role two years from now, what would need to change? That's the question Christy Maxfield (President and CEO at Purpose First Advisors ), Dean Barta (Founder and CEO at Barta Business Group ), and Jess Dewell (Managing Partner and Growth Strategist at Red Direction ) explore in this It's Your Business episode. These three business advisors talk about the mindset shifts and pract...

"Stamina is a trap." Most small business owners already know it. But knowing it and actually building a business that doesn't depend on your constant intervention are two very different things.   We've normalized the grind,  the packed schedule, the heroic push through chaos, the belief that if you just work harder, longer, the growth will come. And somewhere in all that muscling through, we stopp...

"Good ideas come to me easily." It sounds almost too simple. But what if your creativity isn't actually the problem - what if it's the way you've been trained to chase it?   We've built entire careers around productivity systems, packed calendars, and the belief that output is the measure of value. And somewhere in all that busyness, we lost the thing that actually drives innovation: the ability t...