Rise Above The Grind

In this episode of Rise Above the Grind, host Alissa Bickar welcomes Adam "AAA" Adams, a prolific entrepreneur and real estate investor, for a conversation on what the grind really means, how seasons of hard work lead to freedom, and the lessons of building wealth through real estate and business.

Adam grew up in Utah with a stepdad who was a lifelong real estate investor and business owner, and who drilled one rule into him early: save 10%, invest 10%, pay yourself first. A $100 gift of land in college turned into a 12,000%-plus return and the start of Adam's own investing journey, which has included raw land, multifamily, and syndications since 2007. Today he runs a couple of businesses, has two kids, and is serving as the main salesperson for an assisted living community with 25 locations in Colorado.

The show opens with the grind question, and Adam's answer sets the tone for the conversation: the grind isn't something to avoid, but it is something to keep temporary.

Redefining the Grind: A Season, Not a Life Sentence Adam describes the grind as both positive and negative, and above all seasonal. To him, grinding is buckling down and doing what you need to do for as long as you need to do it to get the outcome you want. For Adam, that outcome is tranquility, freedom, starting something new, and time for mountain biking, surfing, and snowboarding.

Don't Avoid the Grind, but Don't Live in It Adam argues that people who avoid the grind entirely are often the ones who end up stuck. At the same time, he hopes people aren't choosing 60, 80, or 90 hour work weeks for their entire lives, because life has more to offer. Alissa highlighted the rhythm in his answer: the grind is part of a cycle, not a destination, and when it defines everything, it depletes you and throws the rest of life out of balance.

The $100 Piece of Land In 2005, Adam's stepdad gifted him a piece of land and, on his accountant's advice, asked for $100 in return so the gift wasn't taxed heavily. As a college student working as a bartender, even $100 took a while to come up with. Two years later, a random call from a buyer offered more than he would have earned in a full year after graduating. The result was a return of more than 12,000 percent on his $100, and the moment he decided his stepdad had been right all along.

Lessons from a Real Estate Family Adam's stepdad has invested in raw land, agricultural land, storage units, multifamily, single family, and cabin lots, and often recommended Robert Kiyosaki's Rich Dad Poor Dad when it came out in 1997. Adam admits he thought the book was ridiculous at the time. He has been investing in raw land since 2005 and in multifamily and syndications since 2007.

Working a 40-Plus Hour Week by Choice After years of running his own businesses on far fewer hours, Adam has spent the last nine months working for a friend as the main salesperson for an assisted living community with 25 locations in Colorado. He describes the shift to more than 40 hours a week as crazy, but says he loves it and plans to stay for another year.

"To me, grinding is buckling down and doing what you need to do for as long as you need to do it in order to get the outcome that you're really looking for." — Adam Adams

"I think it's seasonal." — Adam Adams

"I don't think people should avoid the grind at all, because I think that's why there's a lot of people that are really, really stuck." — Adam Adams

"Life has more to offer than that." — Adam Adams

Rise Above the Grind broadcasts live every Thursday at 12:30 PM Eastern, hosted by Alissa Bickar (The Consultress) in partnership with The No More 9 to 5 Club. Each episode is a mastermind-style conversation designed to help entrepreneurs think differently, build authentic brands, and grow beyond the grind.

In this live broadcast and VIP mastermind edition of Rise Above the Grind, host Alissa Bickar ("The Consultress") reunites with business advisor and author Willard Barth, alongside co-host Jason McNamara and a powerhouse panel featuring Romaine Wright, Tommy Giorlando, Jess Jorgensen, Jen Carpenter, and Talmar Anderson.

Returning to the show nearly a year after his first appearance, Willard unpacks how the definition of "the grind" has fundamentally transformed—shifting from an exhausting badge of honor to the privilege of taking aligned steps toward an intentional vision. The room engages in a deep, unfiltered discussion on the ongoing fallout of global disruptions, shedding outgrown identities, holding "funerals" for legacy projects, and avoiding the trap of mistaking generative AI rapport for genuine, battle-tested wisdom.

Key Takeaways

The Lingering Disruption of Past Assumptions: Many business owners continue operating on pre-2020 assumptions of normalcy. Acknowledging that buyer behaviors, communication channels, and personal boundaries have permanently shifted is essential to avoid stagnation.

Mistaking Knowledge for Wisdom: While generative AI provides instantaneous access to information, it is engineered to build rapport and confirm existing biases rather than provide objective truth. True business strategy requires testing knowledge through real-world experience, trusted peer masterminds, and custom system prompts that challenge assumptions.

Rigid Flexibility & Immutable Laws: Longevity in entrepreneurship relies on establishing immutable, non-negotiable core values while maintaining extreme flexibility in execution. Leaders must remain rigidly committed to their desired outcome while adapting their path.

Holding "Funerals" for Past Selves and Projects: Growth demands the courage to "kill your darlings". Holding onto projects or past versions of yourself simply because you invested time, money, or sweat equity into them robs you of the future you are meant to build.

Extreme Ownership (Phase Three): True personal and operational freedom begins the moment you stop blaming outside circumstances—the economy, parents, or clients—and fully own that past decisions created your current reality, giving you full agency to choose your next steps.

Panel Discussion Highlights

The Post-Disruption Paradigm: Alissa and Willard discuss why businesses and leaders are still navigating the ripple effects of the 2020 pandemic on consumer psychology and workforce expectations.

The Trap of Abdicating to AI: Exploring why automated feedback loops and confirmation bias create echo chambers, and how entrepreneurs can prompt AI to serve as a critical thinking partner instead of a "yes-man".

Immutable Laws in Practice: Romaine Wright breaks down how establishing measurable personal and operational rules acts as a North Star when redefining client avatars and navigating industry noise.

Emotional Conditioning and Truth-Telling: Tommy G explains how subconscious emotions dictate whether we accept or reject constructive criticism, emphasizing the need to drop ego when receiving candid feedback.

Leaving the Wrong Rooms: Jess Jorgensen shares a real-time story of walking away from an industry conference after realizing the culture no longer aligned with her personal values and mission.

Reinventing the Operator: Willard, Jason, and Alissa examine the necessity of shedding former identities, letting go of non-performing initiatives, and refusing to cling to who you were yesterday.

Synthesis & Action: Jen Carpenter and Talmar Anderson provide masterclass takeaways on the power of choice, deliberate action, and narrowing focus down to a singular, linear identity for maximum return on investment.

Featured Resources & Community Links

Community Movement: Join the "I Believe in You" movement (wear one, share one wristbands available via Venmo @TheConsultress).

VIP Live Broadcast Access: Apply to be part of the live studio audience and mastermind panel for Rise Above the Grind via the No More 9 to 5 Club network.

Broadcast Schedule: Catch Rise Above the Grind live every Thursday at 12:30 PM Eastern Time.

In this candid and unscripted broadcast of Rise Above the Grind, host Alissa Bickar ("The Consultress") and No More 9 to 5 Club founder Jason McNamara explore the hidden emotional toll of entrepreneurship: the grind beneath the grind.

Prompted by a last-minute schedule shift due to a guest's family loss, Alissa and Jason dive into the reality of "failure fatigue," processing grief when projects or partnerships fall flat, and recognizing the seasonal necessity of "killing your darlings" to make room for growth. They are joined by veteran entrepreneur Tim Miller, founder of Puddles Be Gone, who shares his raw journey of transitioning from 31 years of assembly-line conditioning at Chrysler to self-taught fluid dynamics, spending nearly a year re-engineering his product from scratch against popular advice, and ultimately catching the eye of national retail buyers.

Key Takeaways

The Reality of Failure Fatigue: Behind promotional social wins lies the 90% of the iceberg that goes unseen. Compounded rejections, stalled launches, and deal fallout cause an internal soul-grind that requires intentional grief and mental renewal rather than simply "shaking it off".

Fall as a Season of Pruning: Growth is not an endless launch cycle. Just as trees shed leaves, high-performing operators must routinely audit their businesses to weed out systems, offerings, and legacy relationships that are "good enough" but incapable of carrying them into the next tier of scale.

Alignment Precedes Marketing: True business clarity comes from leading with authentic attraction and alignment rather than downstream copy. When your core offer and values align, your marketing message becomes clear naturally.

The Discipline of Quality Over Convenience: Tim Miller demonstrates that when consumer feedback reveals product friction, settling for an inferior model ruins long-term enterprise value. Taking the time and capital hit to redesign his base cap from scratch (creating "Blue 2.0") opened institutional interest from major national chains like PetSmart and Tractor Supply.

Upgrading Your Circle and Navigating Separation: Moving away from a scarcity mindset requires curating a circle of growth-oriented peers. When friends or legacy networks fail to understand your vision, seeking out aligned mentors and masterminds provides the courage needed to navigate isolation.

Timestamps & Episode Highlights

– Green room check-in, audio setup, and prepping the broadcast.

– Setting the stage: Addressing the last-minute pivot and opening a discussion on grief and resilience.

– Welcome to *Rise Above the Grind: Defining "failure fatigue" and the 90% of the iceberg under the waterline.

– Jason on military lessons: Failing fast, failing forward, and shedding scarcity thinking.

– The seasonal audit: Why October marks the time to prune projects, systems, and old habits.

– Jason’s boundaries: Handling bad actors, integrity breaches, and protecting the community garden.

– Leading with alignment: Why Alissa shifted focus from marketing tactics to upstream resonance.

– Tim Miller’s transition: Unlearning 31 years of Chrysler assembly-line conditioning.

– The Puddles Be Gone breakthrough: Noticing customer friction and refusing to sell a subpar product.

– Engineering without a safety net: A 6- to 9-month redesign that unlocked national retail conversations.

– Overcoming the pain of separation: Finding a new tribe when lifelong friends don't understand your business.

– Unlocking the *Personal Freedom Blueprint: Generosity, mentorship, and resources for veterans and civilian operators.

– Save the date: Alissa previews her half-day year-end review workshop on November 6th.

– Post-show debrief: Planning community masterminds, StreamYard vs. Zoom multi-streaming, and email list segmentation.

Featured Resources & Community Links

Featured Product: PuddlesBeGone.com – Clean, spill-free watering solutions for messy pets (Version 1 clearance and the upgraded Blue 2.0).

Community Assessment: Access the Personal Freedom Blueprint at nomore9to5club.org to map your path to financial and operational freedom.

MindTrainer PRO: Download from the App Store or Google Play for cognitive clarity, entrainment, and focus.

Save the Date: Mark your calendars for Alissa Bickar’s half-day Year-End Business Review Workshop on November 6th.

Alissa welcomes Tim Grimmett — a residual income mentor who spent years building (and nearly losing) real estate businesses before rebuilding his life around clearer priorities. The conversation opens with the show's signature icebreaker — what does "the grind" mean to you? — and moves into a deep, personal conversation about priorities, faith, loneliness in entrepreneurship, self-sabotage, and the value of true community. The VIP panel adds perspective on niching down, the statistics behind entrepreneurial isolation, and personal growth through discomfort.

1. "The American Dream Gone Wild" Tim opens with a redefinition of the grind: the traditional path (school, job, house, retirement) that turned into a trap for him — sacrificing what mattered most in pursuit of keeping up with others.

2. Losing It All and Rebuilding Tim shared candidly about running 7 LLCs and 20 employees before the real estate crash wiped out his financing and nearly cost him his marriage. That crisis became the turning point for reassessing what success actually means.

3. Priorities in Order: God, Spouse, Kids, Work Central to Tim's framework is a clear hierarchy of priorities. He explained that re-ordering his life around this sequence — rather than work first — is what allowed everything else to fall into place.

4. Removing Three Things From Hustle Culture Tim's framework for "doing business a different way" involves removing: avarice (the love of money), loneliness, and hustle at the expense of everything else.

5. The Loneliness of Entrepreneurship — By the Numbers Willard shared research live on the call: only 15–18% of the U.S. population engages in entrepreneurial activity, and just 6.6% run a business that survives more than 3 years — meaning most entrepreneurs are surrounded by people who don't understand their day-to-day reality.

6. Self-Care vs. Self-Sabotage Romaine raised a powerful distinction from her own podcast: what looks like self-care (solitude, long runs, "staying fit") can sometimes be a disguised response to loneliness or avoidance. Tim and Alissa built on this, discussing how entrepreneurs often self-sabotage or shrink back when approaching a new level of growth.

7. Community as the Antidote Tim emphasized that no one is self-made — real growth requires community, encouragement, and people willing to challenge you compassionately. He noted that shedding relationships that no longer serve your growth is often part of leveling up.

8. Niching Down and the Pain of Repositioning Willard shared his own recent pivot — moving away from smaller business clients who intellectually understood their problems but weren't in enough pain to invest, toward a more defined avatar (3–15M in revenue, 10–50 employees) that matched real urgency.

9. Zooming Out: The Artist and the Painting Willard referenced a Steven Tyler (Aerosmith) analogy: entrepreneurs are "6 inches from the canvas" and think everything is perfectly blended, while the people who'd actually buy their solution are standing 6 feet back, seeing something entirely different — a case for outside perspective and community feedback.

Tim Grimmett — Residual Income Mentor

Rise Above the Grind broadcasts live every Thursday at 12:30 PM Eastern. Subscribe at theconsultress.com/podcast to know who's coming up next and get access to the room where it happens.

This episode dug into what actually drives the grind: not just overwork, but the beliefs underneath it. Alissa welcomed James Elliot, who helps coaches, wellness practitioners, and entrepreneurs with ADHD reclaim 15 to 30 hours a week by building businesses that don't run on burnout.

James traced the grind back to programming from parents, culture, and corporate systems that equate hustle with worth. After years in the corporate world and then building a multiple six-figure business that was quietly killing him, he had to confront a hard question: if this is success, why doesn't it feel like it?

James shared the specific moments that forced a change: his body wouldn't respond to a healthy diet and consistent workouts because of chronic stress, a close friend told him he hadn't seen him in nearly a year, and his niece asked if he didn't like the family anymore since he never visited. Each moment pointed to the same truth: the business built for freedom had produced none.

Pain means pay attention. James reframed pain, whether physical, emotional, or relational, as information rather than something to avoid. Ignoring it just delays the reckoning.

Busy is not the same as productive. Several voices in the room, including Jess Jorgensen, pushed back on using constant availability and visibility as proof of value. Exhausted is not a badge of honor.

Delegation is a habit, not a one-time decision. James and Jason both made the case for paying someone else to do the $10-an-hour tasks so you're free to do the $200-an-hour work. The math only works if you actually let go.

Success needs a personal definition. Tommy Giorlando pointed out that most people chasing "success" haven't defined what it actually looks or feels like, which means they're often succeeding in the wrong direction entirely.

Think about your thinking. James closed by challenging the room to question inherited beliefs about needing to earn rest, earn freedom, or earn the right to slow down.

This episode marked the official launch of the I Believe In You movement inside the Rise Above the Grind community, and served as a preview broadcast ahead of the No More 9 to 5 Club Lifestyle Summit. Alissa sat down with speaker coach Toni Caruso, surrounded by an all-star panel of upcoming Summit speakers, for a real conversation about consistency, belief, and building a business around your message.

Toni opened by defining the grind as consistency, especially when no one is applauding you yet. The hard part isn't the big stage moment. It's the daily discipline of moving toward a goal before you have any proof it's working.

Toni traced her path all the way back to childhood, where a summer birthday meant small parties while her sister's spring birthday drew a crowd. That early lesson in promotion turned into a full career: certified event planner, founder of Caruso Signature Events, and eventually managing director for eWomen.

When the pandemic shut down her entire events business overnight in March 2020, Toni invested in a mastermind program that pushed her to focus. Within three months of following that guidance, she built what became the eWomen Speakers Network, coaching speakers on how to turn their message into a business.

Find your through line. Toni encouraged everyone to identify the personal story that connects directly to the work they do now, and to use that alignment as the foundation of their message.

Speaking is a business, not a moment. Toni was direct: know what you want before you walk off stage, whether that's emails collected, book sales, or coaching conversations. Vet every room you're invited into and make sure it's full of the right audience, not just any audience.

Borrow belief until you build your own. Several panelists connected on the idea that self-belief often starts with someone else believing in you first. Braxton and Alissa both pointed to moments where one person's confidence in them created the momentum to take the next step.

Be who you say you are. Toni pushed back on AI-generated headshots and overly polished personas, reminding speakers that trust has to be built before they ever get on stage.

Instagram: @tonicarusoevents

What happens when you stop trying to sound like everyone else and start trusting the voice you already have?

In this episode of Rise Above the Grind, Alissa Bickar sits down with Nat Mailhot, speaking coach, communication educator, and creator of Mastery Authentic Voice, for a lively conversation about finding your voice, building confidence, embracing your personality, and making communication more engaging.

Nat brings a refreshing perspective to speaking: communication doesn't have to feel stiff, serious, or scripted. It can be structured, authentic, playful, and fun.

Her own journey—from being an extremely shy child to becoming a speaking coach and working confidently with both professionals and teenagers—shows how much our identities can evolve when we give ourselves permission to practice, experiment, and speak up.

Nat explains that when she started Mastery Authentic Voice, she built the program around three core ideas:

Communicate clearly.

But there was another essential ingredient:

Make it fun.

After more than 30 years working with children, Nat learned how powerful games, humor, activities, and play can be when helping people step outside their comfort zones.

Instead of making people feel like they're being forced to learn something difficult, she creates an environment where they can relax, participate, experiment, and eventually realize:

“Oh, that wasn't so bad.”

One of the most compelling parts of Nat's story is that she didn't always see herself as a confident communicator.

She describes being extremely shy as a child and eventually adopting the identity others had given her: “She's shy.”

Working with children helped her begin to break through that identity.

Later, becoming a parent gave her an even deeper motivation.

After looking back at her own high school experience while holding her daughter's hand, Nat realized:

“Nobody taught me how to do this.”

She decided she didn't want her daughter to grow up without the communication and confidence skills she needed to navigate the world.

That realization became part of the inspiration behind Teen Talk.

One of the most memorable stories from the conversation involves something incredibly simple:

Ordering a cookie.

Instead of automatically ordering for her daughter, Nat encouraged her to walk up to the counter and ask for what she wanted herself.

That small interaction became a lesson in independence, communication, confidence, and navigating the real world.

And it worked.

Years later, her daughter was confidently ordering for herself—even in Spanish.

The lesson extends far beyond parenting:

Sometimes confidence comes from being allowed to do the uncomfortable thing yourself.

Nat makes an important distinction between being authentic and being unprepared.

Speaking naturally doesn't mean walking into a presentation with absolutely no idea where you're going.

For someone beginning their speaking journey, she recommends having a basic structure:

That structure creates a framework.

With enough practice, the structure becomes second nature, allowing the speaker to become more spontaneous and responsive without losing the audience.

Structure + Practice + Authenticity = Natural Communication

Nat points out that speakers often already have the stories they need.

The key is knowing which story illustrates the point you're trying to make.

Your experiences become part of your communication DNA.

The stories you've told hundreds of times may feel ordinary to you—but to someone hearing them for the first time, they can create an immediate connection:

“That sounds like me.”

And that is where communication becomes powerful.

One of Nat's favorite questions to ask people is:

Maybe it's a message of:

The challenge is to identify that message and then step boldly into what you believe.

Because everyone has something to say.

Sometimes we simply haven't taken the time to discover what our message is.

When people feel relaxed and engaged, they're more willing to learn and experiment.

You don't have to feel confident before taking action. Sometimes the action is what creates the confidence.

You can be completely yourself while still having a structure.

The experiences you've lived through can become the most relatable way to teach someone else.

You don't necessarily need to eliminate the qualities that make you different. You may need to learn how to use them.

Nat's experience on a cruise ship taught her an important lesson: there are ways to disagree, challenge something, and still communicate it well.

The question is whether you're willing to find it—and share it.

“My worth is not defined by my productivity or what I do.”

“It had to be fun, it had to be playful, and it had to have humor.”

“If you could share one message with the world right now, what would that message be?”

“You have to find the gentle balance between natural and a bit of structure.”

“It’s all about connectivity and being relatable.”

“We all have a message to share.”

You don't become an effective communicator by trying to become somebody else.

You become one by knowing your message, understanding your audience, practicing your craft, and giving yourself permission to show up as yourself.

The goal isn't to eliminate every awkward moment.

It's to become comfortable enough with yourself that you can navigate those moments, learn from them, and keep going.

Because sometimes the biggest thing standing between you and your next level isn't a lack of knowledge.

It's simply the courage to use your voice.

What if selling didn't have to feel pushy, awkward, or transactional?

In this episode of Rise Above the Grind, Alissa Bickar sits down with Jeff Goldberg, sales coach, trainer, and founder of the Sales Confidence Lab, for a candid conversation about sales, prospecting, confidence, accountability, and what it really means to serve people through the sales process.

With 50 years of professional sales experience and experience training tens of thousands of salespeople, Jeff brings a practical perspective to one of the biggest challenges facing entrepreneurs, consultants, coaches, and small business owners: learning how to sell when selling isn't the reason you started your business.

Sales is service.

Jeff's central philosophy is simple: when you're selling, your goal shouldn't be to pressure someone into buying. Your goal should be to determine whether you can genuinely help them.

Sometimes serving someone means making the sale. Sometimes it means telling them you're not the right person and connecting them with someone who is.

You can't serve enough people if you're not talking to enough prospects.

Consistent and effective prospecting is a necessary part of building a sustainable business. Waiting for the phone to ring isn't always enough.

Ask better questions.

Jeff challenges the idea that great salespeople win because they have incredible presentations or closing techniques. Instead, effective selling starts with understanding the prospect, asking thoughtful questions, and uncovering objections early.

Don't chase people who don't want to be chased.

Jeff emphasizes working with people who are interested, responsive, and willing to keep the process moving forward. Your time is valuable, and not every prospect deserves unlimited follow-up.

Accountability can turn intention into action.

A simple accountability partnership can help entrepreneurs consistently follow through on their prospecting commitments without requiring complicated systems.

Are you consistently talking to enough people who could benefit from what you do?

And perhaps the bigger question:

What would change in your business if you stopped thinking of sales as “closing” and started thinking of it as serving?

Jeff Goldberg is a sales coach and trainer with 50 years of professional sales experience. He has worked with organizations including Cisco Systems, Siemens, Aramark, State Farm, and Citibank, and has trained tens of thousands of salespeople around the world.

He is the creator of the Sales Confidence Lab, a 12-week program designed specifically for “accidental salespeople”—coaches, consultants, entrepreneurs, solopreneurs, and other professionals who need to sell but didn't start their businesses because they wanted to become salespeople.

Jeff also brings his experience as a stand-up comedian to his work, making sales conversations practical, energetic, and human.

🌐 Website: jgsalespro.com

00:15 — Meet Jeff Goldberg

19:39 — What Does “The Grind” Mean?

23:31 — Sales Is Service

26:08 — The Prospecting Problem

28:03 — The Long Game of Prospecting

31:00 — The Power of Accountability

36:47 — Handling Objections

37:53 — The Psychology Behind Objections

38:44 — Ask Better Questions

58:20 — Sales War Stories & Difficult Prospects

01:03:32 — Stop Chasing

Final Takeaway — Sell by Serving

What if your book could do more than sit on a shelf?

In this episode of Rise Above the Grind, Alissa Bickar sits down with Keren Kilgore, a publishing maven and founder of Quantum Shift Media, to explore how entrepreneurs can use books as powerful tools for visibility, authority, business growth, and leverage.

Keren shares her perspective on publishing, collaboration, alignment, and the deeper work required to create a book that genuinely supports the business and life an entrepreneur is building.

Rather than treating a book as simply another product, this conversation explores how your knowledge, experiences, and message can become an asset that opens doors and creates opportunities.

Don't just publish a book. Build an asset.

The right book can become an extension of your expertise—creating credibility, opening conversations, attracting opportunities, and giving your business another way to communicate its value.

Keren explains that her publishing process begins with alignment, bringing the author's conscious and subconscious intentions into greater alignment before moving into the publishing process.

Keren Kilgore is a publishing and marketing expert who helps authors write, publish, and market books designed to create meaningful business transformation. Through Quantum Shift Media, she works with entrepreneurs to turn their knowledge and ideas into books that can become powerful business leverage.

Rise Above the Grind is a conversation series for entrepreneurs and professionals who are ready to question what is no longer working, rethink conventional approaches, and create better careers and lives moving forward. The show focuses on conversations from the growth edge of successful entrepreneurship and turning those insights into practical action.

Keren Kilgore / Quantum Shift Media

Host: Alissa Bickar

Keren Kilgore, Keren Kilgore publishing, Quantum Shift Media, book publishing for entrepreneurs, author marketing, writing a business book, publishing a book, entrepreneur books, business leverage, intellectual property, personal branding, entrepreneur visibility, business growth, aligned entrepreneurship, Rise Above the Grind, Alissa Bickar, entrepreneur mindset, author strategy, business transformation.

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