This episode of The Art of Entrepreneurship is for anyone who’s ever hit a wall in their career and wondered what it would take to rebuild something even bigger.

My guest is Ilana Golan, tech entrepreneur, performance coach, and founder of Leap Academy. Ilana and I discuss her journey from the Israeli Air Force to Silicon Valley, where she learned that the biggest cost in life isn’t what you spend—it’s the money (and potential) you’re not making.

Tune in for practical insights on getting leap-ready, recognizing self-imposed barriers, and creating a career that compounds over time.

⭐ Feeling inspired to take your next leap? Visit leapacademy.com for Ilana’s free Career 360 training and strategy session invitation.

Ilana Golan is a tech entrepreneur, performance coach, and founder of Leap Academy—recognized by Inc. Magazine as one of the fastest-growing companies in the U.S. A former Israeli Air Force officer and Silicon Valley engineer, Ilana helps high performers elevate their leadership, build portfolio careers, grow their personal brands, and create meaningful impact on their own terms.

Website: https://www.leapacademy.com/

LinkedIn - IIana Golan: https://www.linkedin.com/in/ilanagolan/

LinkedIn - Leap Academy: https://www.linkedin.com/company/leapacademy-global/

Instagram: https://www.instagram.com/ilanagolanleap/

YouTube: https://www.youtube.com/channel/UCLcQtEE8dmUFB-KF1NaVhVQ

• Overcome doubts w/ Kara Goldin, Founder & CEO of Hint, Inc.: https://www.jackiehermes.com/podcast/kara-goldin-rebroadcast
• My entrepreneurial journey: https://www.jackiehermes.com/podcast/my-entrepreneurial-journey
• Turning pain into power w/ Gregory Proctor, management executive, entrepreneurial leader and author: https://www.jackiehermes.com/podcast/gregory-proctor

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

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This episode of The Art of Entrepreneurship is for anyone who’s been told they need to be a “visionary founder”—but knows execution is where the real work happens.

Today I'm talking about why being visionary without execution is wasted potential, the unsexy truth of entrepreneurship, and the habits that keep founders chasing shiny new things instead of finishing what they start.

Tune in to learn how to shrink your vision into daily actions, build accountability rhythms, and measure progress—not motion—so you can actually deliver on your ideas.

• What I learned from my first (vegan cookie) company (revisited): https://www.jackiehermes.com/podcast/my-first-company-revisited
• Becoming a successful entrepreneur: credibility, first customers, scaling & fundraising w/ Yoav Vilner, Co-founder & CEO of Walnut: https://www.jackiehermes.com/podcast/yoav-vilner
• Ideas are nothing without execution (revisited): https://www.jackiehermes.com/podcast/ideas-are-nothing-without-execution-revisited

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com

This episode of The Art of Entrepreneurship is for anyone looking for systems to help them manage when everything feels urgent or on fire.

My guest today is Skye Waterson, founder of Unconventional Organisation and an implementation coach for entrepreneurs with ADHD. Skye and I discuss why high-achieving entrepreneurs often go undiagnosed, how to harness ADHD “superpowers” without getting tripped up by their shadow sides, and her step-by-step way to prioritize when you’re crunched for time.

Make sure you tune in for Skye’s science-backed strategies to externalize time, focus on what’s truly urgent, and swap willpower for repeatable systems that protect your energy and fuel sustainable growth.

⭐ If this resonates with you, don’t miss this free resource: DM Skye on Instagram with the word “AOE” to get her playbook!

Skye Waterson is the founder of Unconventional Organisation, a multi–six-figure business dedicated to helping entrepreneurs with ADHD (or suspected ADHD) build systems that actually work for their brains. She leads a team of neurodiverse coaches who work with clients worldwide—including those with ADHD, ADD, ADHD+ASD, and chronic disorganisation—to create tailored systems that make consistency easier, reduce overwhelm, and unlock sustainable growth.

Website: https://www.unconventionalorganisation.com/

LinkedIn - Skye Waterson: https://www.linkedin.com/in/skye-waterson-026286204/

LinkedIn - Unconventional Organisation: https://www.linkedin.com/company/unconventional-organisation/

Instagram: https://www.instagram.com/unconventionalorganisation/

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com

This episode of The Art of Entrepreneurship is for anyone who’s ready to stop letting chaos dictate the quality of their work.

We’ve all experienced it: last-minute requests, unrealistic timelines, and the chaos that comes when others don’t think ahead. In this episode, I talk about why rushed work rarely leads to great results, how constantly scrambling chips away at your standards, and the hard truth that you get what you accept.

Tune in to hear real examples of what boundary-setting can sound like, why pushing back matters, and how to reclaim your time so you stop sacrificing your happiness for someone else’s lack of planning.

• All customers are not good customers: https://www.jackiehermes.com/podcast/all-customers-are-not-good-customers
• When is the sacrifice too much?: https://www.jackiehermes.com/podcast/when-is-the-sacrifice-too-much
• The hard way isn't always the right way: https://www.jackiehermes.com/podcast/the-hard-way-isnt-always-the-right-way

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com

This episode of The Art of Entrepreneurship is for anyone who loves being an entrepreneur—and wants to be known for more than just that role.

My guest today is Michael Fabiano—world-renowned opera singer, pilot, nonprofit founder, and a tech partner building a smart CRM for entertainment venues. Michael and I dig into what it means to break free from labels, why chasing multiple passions can actually make you sharper in each, and the discipline it takes to manage them all.

Make sure you tune in for Michael’s insights on effectiveness, efficiency, and the pursuit of excellence over “good enough”—plus the one rule he lives by: don’t wait in line in life, move when opportunity shows up.

Michael Fabiano is an international musician who has performed leading roles around the world in major opera theaters. He is the President and Co-founder of ArtSmart, a national nonprofit providing free one-to-one music mentorship for under-resourced students. He is also the Chief Business Development Officer at Resonance, a social commerce platform that provides creative professionals and organizations with the mechanism streamline operations, modernize financial systems, and grow their business. A recipient of the Beverly Sills and Richard Tucker Awards, Michael brings the same discipline, focus, and pursuit of excellence from his artistic career into his work as an entrepreneur and leader.

Website: https://michaelfabianotenor.com/

Resonance: https://www.resonanceglobal.com/

ArtSmart: https://pattihuppmusic.com/foundation/

LinkedIn https://www.linkedin.com/in/michael-fabiano-19a05a2b/

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com

This episode of The Art of Entrepreneurship is for anyone who feels conflicted when asked: do you need a vacation, or an escape?

There’s a difference between running away from your life and taking a break to recharge. In this episode, I share how I’ve confused the two in the past, what it signaled about the way I was working, and the mindset shift that helped me build a life I don’t want to run from.

Tune in to reflect on what a meaningful break looks like for you, and how small daily choices can build a life you truly love.

• Driven or drained? Scaling a company without burnout: https://www.jackiehermes.com/podcast/driven-or-drained
• Stop being your own greatest enemy: https://www.jackiehermes.com/podcast/your-own-worst-enemy
• Your thoughts become your reality w/ author & health coach Justine Sloan: https://www.jackiehermes.com/podcast/manifesting-with-justine-sloan

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com

This episode of The Art of Entrepreneurship is for anyone who’s curious about what truly sets successful CEOs apart—and how to grow into the kind of leader your team needs.

My guest today is Patrick Thean, bestselling author, entrepreneur, and CEO coach. Patrick founded his first company in his 20s and landed it on the Inc. 500 list, and for the past few decades he’s been coaching high-performing CEOs around the world.

Patrick and I get into everything from what differentiates successful leaders, to what he’s learned about himself through decades of coaching, to the daily rhythms and practices that help CEOs build strong, successful teams.

Make sure you tune in for actionable advice on humility, curiosity, feedback, and the mindset shift from doing to thinking—insights every leader can use (and a few I hadn’t heard before!).

Check out Patrick’s bestselling books: https://www.rhythmsystems.com/patrick-thean/books

Patrick is an award-winning entrepreneur, USA Today bestselling author and world-renowned strategy execution expert. He is the mastermind behind the Think Plan Do® process, a CEO coach, serial entrepreneur, and the co-founder of Rhythm Systems®. He speaks and writes on topics such as leadership, strategic planning, and team accountability, in addition to coaching CEOs and their executive teams.

• Website https://www.rhythmsystems.com/patrick-thean
• LinkedIn – Patrick https://www.linkedin.com/in/patrickthean/
• LinkedIn – Rhythm Systems https://www.linkedin.com/company/rhythm-systems-inc/
• Books https://www.rhythmsystems.com/patrick-thean/books

• Embracing intellectual humility w/ Dave Hersh, Founder & CEO of In Tandem: https://www.jackiehermes.com/podcast/dave-hersh-ceo-of-in-tandem
• Unapologetic ambition w/ Vicky Boudreau, co-founder and CEO of Heylist: https://www.jackiehermes.com/podcast/vicky-boudreau-co-founder-ceo-of-heylist
• Stop overworking and underliving w/ The Entrepreneur Coach Bri Seeley: https://www.jackiehermes.com/podcast/bri-seeley

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on

This episode of The Art of Entrepreneurship is for anyone who needs the reminder to look back, take stock of how far you’ve come, and celebrate your wins.

As part of our summer rebroadcast series, I’m revisiting the story of my very first company—a vegan cookie business I started over a decade ago. (Cookies, sounds fun! But it was hard.) I shared this story more when I first started Accelity, and going back to it now was a cool walk down memory lane.

We’re so often focused on the next goal or milestone that we forget to pause and appreciate the progress we’ve made. The version of you from 10, 5, or even 2 years ago would be so proud of where you are today.

Spoiler: this isn’t going to be some amazing unicorn success story, but I learned a ton from that first venture. Tune in for three important lessons on entrepreneurship.

• Do you have founder’s syndrome? Overcoming it with Erica Rankin, founder of Bro Dough: https://www.jackiehermes.com/podcast/founders-syndrome-with-erica-rankin
• Hiring friends and family: https://www.jackiehermes.com/podcast/hiring-friends-and-family
• My entrepreneurial journey: https://www.jackiehermes.com/podcast/my-entrepreneurial-journey

✨ This podcast is produced in partnership with Accelity, a full-service marketing agency for bold people growing bold companies.

If you're ready to level up your B2B marketing, check us out.

→ accelitymarketing.com

🎧 Catch up on past episodes, submit topic ideas, and learn more

jackiehermes.com/podcast

⭐ Love what you hear? Please leave a 5-star rating on Spotify and on Apple Podcasts to help more entrepreneurs find the show.

📲 Let’s connect!

LinkedIn: linkedin.com/in/thejackiehermes/

Instagram: @thejackiehermes

TikTok: @jackie.hermes

Website: jackiehermes.com