This week in the guest chair, we have someone very special, my sister, Nadeen Matthews Blair and her pivot story is going to speak directly to anyone who’s ever felt called to reinvent themselves.

After 20 years in banking, management consulting, and C-suite leadership, Nadeen hit a point where the titles, the pressure, and the nonstop demands were no longer aligned with the life she wanted for herself and her family. So she did what so many high-achieving women fear doing: she stepped back, listened to the whisper, and chose a new path.

That path led her to Crescent Advisory Group, where she now teaches professionals, creatives, and new entrepreneurs how to use AI with confidence. What’s wild is that she built the entire business using just four beginner-friendly AI tools and today, she’s breaking them all down for you.

Whether you’re in a pivot, launching a side hustle, or trying to understand where AI fits into your next chapter, this episode will give you clarity, confidence, and a simple starting point.

In This Episode, Nadeen Shares:

• How she pivoted from a demanding corporate career into full-time entrepreneurship
• Why early consulting and workshop opportunities found her before she officially launched
• How AI tools like Perplexity, Gamma, Looka, and Namelix helped her build her brand, website, and business foundation fast
• Why AI is the most powerful leverage tool for side hustlers in 2025
• How redefining success around flexibility, family, and purpose shaped her new chapter
• What she’s teaching thousands of people in her beginner-friendly AI webinars

If you’ve been feeling the pull to pivot or you’re curious about how to use AI without feeling overwhelmed, this is your episode.

Watch Episode 489 on YouTube and listen on all podcast apps.

Links mentioned in this episode

Crescent Advisory Group: http://crescentadvisorygroup.com

ChatGPT

Perplexity

NameLix

Gamma

Lovable

MIT AI Courses

Alicia Little’s AI Innovation Program

Side Hustle Pro – @sidehustlepro: https://www.instagram.com/sidehustlepro/

Nadeen Matthews Blair IG: https://www.instagram.com/nadeenmatthewsblair/

Nadeen Matthews Blair LinkedIn: https://www.linkedin.com/in/nadeenmatthews/

Hosted on Acast. See acast.com/privacy for more information.

This week in the guest chair we have Keewa Nurullah, artist, entrepreneur, and small-business strategist you may remember as the founder of Kido, the beloved South Loop children’s boutique that brought color, culture, and community to families across Chicago.

After six powerful years in business, and national recognition that included a shout-out from President Barack Obama, Keewa made the bold decision to close her brick-and-mortar store and start over.

In this episode, Keewa opens up about what it truly looks like to evolve as an entrepreneur, navigating economic shifts, changing customer behavior, and the emotional side of letting go of something you built from the ground up. Today she’s channeling those lessons into her work as a strategist and host of Circulate, a monthly community event that “love-bombs” local shops with intentional support and helps other founders build thriving, purpose-driven businesses on their own terms.

In this episode, she shares:

• The courage to walk away from a business 
• What retail taught her about leadership, money, and boundaries
• The realities of pivoting after success
• How she’s creating new pathways for community-minded entrepreneurs

00:00 Intro

03:10 Launching Kido and building community through culture

08:45 Getting national recognition (including Barack Obama’s shout-out)

13:20 The moment she knew it was time to close her storefront

17:15 Navigating shifting customer habits post-pandemic

22:40 Starting over as a strategist and redefining success

27:00 Creating Circulate and supporting small businesses

33:15 Lessons on resilience, rest, and rediscovering your "why"

40:00 Advice for entrepreneurs in transition

Watch episode 488 on YouTube and listen on all podcast apps

Links mentioned in this episode

• Keewa Nurullah Instagram:@kiwimercury
• Keewa’s website: https://www.keewanurullah.com/
• Side Hustle Pro: https://sidehustlepro.co

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebook

Instagram: @kiwimercury

Hosted on Acast. See acast.com/privacy for more information.

This week we’re diving into how to shift your mindset to set yourself up for success. Here’s the thing I’ve learned over the years that your mindset isn’t just a nice-to-have; it’s the foundation for everything you’re trying to build. Whether it’s pushing past fear to finally launch your business, staying consistent when sales are slow, or silencing that little voice in your head saying, ‘Who are you to do this?’ it all comes back to how you think and how you show up for yourself.

In this episode I share:

• The mindset hacks I use, like reframing limiting beliefs, to conquer my goals 
• How to break down your goals into actionable steps to avoid overwhelm 
• My experience with imposter syndrome and how I continuously overcome it

Highlights include:

• 00:00 Intro
• 01:00 Battling imposter syndrome
• 04:14 Breaking free from overthinking
• 08:05 Confidence is key
• 14:05 Master Instagram Challenge
• 17:50 Building mental resilience 
• 21:28 Actionable steps to a mindset change

Check out episode 487 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube

Links mentioned in this episode

• Side Hustle Pro YouTube: https://www.youtube.com/@SideHustlePro 
• Side Hustle Pro Instagram: https://www.instagram.com/sidehustlepro/ 
• SHP Done Is Better Than Perfect Episode: https://www.youtube.com/watch?v=naMuG3Abzmo 
• SHP Denise Woodard Episode: https://www.youtube.com/watch?v=wjQqNBd8-xA 

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

Welcome back to the Side Hustle Pro podcast, your headquarters for turning passion projects into profitable businesses! I’m Nicaila, and today we’re talking about how to find (and protect) the time you need to build your side hustle. 

I get it: Working a full-time job, juggling family commitments, and trying to live your life can make your side hustle goals feel impossible. But trust me, it’s not. I used to think I had zero free hours, but as soon as I did a reality check, I found pockets of time I could reclaim. Here’s how you can do the same.

In this episode I share about:

• The time you’re losing and how to identify your top time wasters
• The 3-Step Hustler’s Time Plan: how to maximize your time
• How to build a system and schedule that work for you

Highlights include: 

• 00:00 Intro
• 01:45 Identify your biggest time traps
• 06:42 Reclaim your time
• 12:35 Power hour: get more done in less time
• 16:15 Leverage your days off
• 18:30 Protect your side hustle hours
• 21:20 Choose a schedule that fits your life
• 23:40 Final thoughts and recap

Check out episode 486 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube

Links mentioned in this episode

• Nicaila’s Website: https://sidehustlepro.co/
• Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ 
• Nicaila’s LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome 
• Brown Ambition Podcast: https://brownambitionpodcast.com/ 

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

Always wanted to start a side hustle but didn’t know what industry to try? This week I’m breaking down the exact process of identifying the skills you do effortlessly and turning them into a profitable side hustle. 

In this episode I share:

• How to pinpoint the skills hiding in your “blind spot”
• The importance of surveying your network to confirm your strengths
• Different service-based ideas you can launch today
• How to validate your offers quickly and start getting paid sooner

Highlights include:

• 00:00 Intro
• 02:00 Three key steps
• 05:30 Monetizable skills
• 09:30 How to get paid sooner, not later
• 15:00 Actionable homework

Check out episode 485 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube

Links mentioned in this episode

• Portia Obeng SHP episode: https://youtu.be/4qkgObsQ7pA?si=BySviTQaeTqgVa01 
• Nicaila’s Instagram: https://www.instagram.com/sidehustlepro/ 
• Nicaila’s LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome 
• FREE Survey Template: https://sidehustlepro.lpages.co/side-hustle-survey/  

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: https://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

This week we’re airing my first ever live podcast! I had the opportunity to sit down with author, journalist, and media powerhouse Demetria Lucas at the On Air Fest in Brooklyn, NY. 

From launching A Belle in BK to building an empire that spans books, film, podcasting, and more, Demetria has mastered the art of evolving and thriving as a multi-hyphenate entrepreneur. Taking risks and flawlessly pivoting has paid off.

In this episode she shares:

• How prioritizing steady income through podcasting, owning a travel company, and more gives her freedom to enjoy life outside of working
• The enormous impact traveling the world has had on her work, leading her to author three books on travel 
• How she stayed resilient through personal challenges and self-doubt

Highlights Include:

00:00 Intro

03:36 Breaking into the book industry

08:20 Streams of steady income

13:45 Building a personal brand and podcast

24:08 Traveling the world

27:00 The ups and downs of finances in freelancing

36:15 Tips for entrepreneurs 

Check out episode 484 of Side Hustle Pro podcast out now on Apple Podcasts, Spotify, and YouTube

Links mentioned in this episode

• Demetria’s Website: https://www.demetriallucas.com/ 
• Demetria’s Instagram: https://www.instagram.com/demetriallucas 
• Demetria’s Facebook: https://www.facebook.com/demetriallucas 
• Ratchet and Respectable Podcast: https://podcasts.apple.com/us/podcast/ratchet-respectable/id1449001372 
• TikTok: https://www.tiktok.com/ 

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

In this solo episode, I’m sharing the first three moves I’d make if I were starting a side hustle today and it’s not what you think.

Over the years, I’ve seen so many new side hustlers get caught up in the wrong things (logos, websites, Instagram aesthetic), and miss the real work that actually builds momentum and income. So I’m breaking down what I’d focus on right now if I had to start all over again.

These are the same foundational steps that helped me build Side Hustle Pro from an idea into a full-fledged business, and they’re the same ones I teach my clients today.

In this episode, I share:

• The number one mistake new side hustlers make (and how to avoid it)
• How to get laser-focused on the problem you solve and who you serve
• Why validation calls will change the way you approach your business
• The difference between a website and a funnel (and why the latter matters more)
• How I started selling a $50 course before I ever built a website

00:00 Intro

02:10 Getting clear on the problem you solve

06:00 Finding your target audience

08:36 Validating your idea fast

11:09 What to ask during validation calls

14:41 Pricing with confidence

15:00 Building a simple funnel, not a website

19:03 How one simple email list changed everything

21:02 Recap: The 3 moves to start your side hustle today

• Leadpages
• Fireflies.ai – My favorite meeting note-taker
• Gemini for Google Meet

Join our Facebook Community

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

Being out of work can feel scary, the bills don’t stop, and self-doubt creeps in. But here’s the thing: this doesn’t have to be the end of your story. It can be the beginning of your expansion. Today, I’m sharing seven side hustles you can start right now to rebuild your confidence, earn income, and remind yourself that you have options.

Each of these hustles has the potential to bring in quick cash this month or grow into a long-term business. Momentum builds confidence, and confidence builds opportunity. 

• Seven side hustles you can start right now if you’re unemployed or need extra cash—from digital products to service-based opportunities.
• How to use your existing skills and everyday tools like Canva, ChatGPT, and social platforms to quickly generate income.
• Why momentum matters more than perfection, and how even a small win can rebuild your confidence.
• The importance of direct outreach—emails, texts, and personal asks—when you need to make money fast, instead of relying solely on social media.

• 00:00 Intro
• 02:20 Side Hustle #1: Career Story Studio
• 04:40 Side Hustle #2: Digital Templates Shop
• 07:06 Side Hustle #3: TikTok Shop Seller
• 09:29 Side Hustle #4: Airbnb Co-Host
• 13:59 Side Hustle #5: UGC Creator
• 16:20 Side Hustle #6: AI Consultant
• 18:44 Side Hustle #7: Fractional Ops Manager
• 23:28 Final thoughts on making money now
• 25:32 Closing thoughts + live class invite

• Register for my free class: Start the Podcast That Builds Your Exit Plan: https://sidehustlepro.co/freetraining
• 
  

Side Hustle Pro – @sidehustlepro

Side Hustle Pro Nicaila Matthews Okome

Hosted on Acast. See acast.com/privacy for more information.

For a long time, I believed pivoting meant I had failed. But now, I’ve learned that pivoting is actually proof that you’re still growing, still expanding, and still in motion.

In this episode, I open up about why I recently applied for a job, how it connects to everything I’ve built with Side Hustle Pro, and the lessons I’m learning in this new season.

In this episode, I share:

• Why pivoting is feedback, not failure
• How every pivot stacks and nothing is wasted
• The dangers of comparison and how to release shame
• Why pivots prepare you for your next expansion season

Highlights include:

00:00 Intro

02:20 What pivoting really means

07:05 Why I applied for a new role

11:45 Lessons from past pivots that shaped Side Hustle Pro

16:20 How comparison creates false shame

20:59 Why pivots keep you in motion

25:00 The role of podcasting in creating new opportunities

28:00 Closing thoughts + live class invite

Watch episode 481 on YouTube and listen on all podcast apps

Links mentioned in this episode

• Register for my free class: https://sidehustlepro.lpages.co/your-first-1000-downloads/

Announcements

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebook

Click here to subscribe via RSS feed (non-iTunes feed): sidehustlepro.libsyn.com/rss

Social Media

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.

In this solo Expansion Era episode, I’m opening up about a turning point in my journey: when I realized my life was running me, not the other way around. I share the step I took to shift that dynamic and the five powerful lessons that continue to guide me today. From building discipline like a muscle, to falling in love with the process, to tracking effort over outcomes, these lessons are helping me reclaim balance, confidence, and control. I’m still in the process myself, but I know these insights can help you start running your life, too.

In this episode I share:

• Why focusing on the muscle you’re building matters more than the result
• How to fall in love with the process and romanticize the mundane
• The importance of tracking the process, not just the outcomes
• How to recognize and adjust for your shortcomings
• Why letting go of rigid expectations opens the door to more wins

Highlights include:

• 00:00 Intro
• 02:26 Lesson 1: Focus on the muscle, not the results
• 07:12 Lesson 2: Fall in love with the process
• 11:24 Lesson 3: Track the process, not the result
• 16:05 Lesson 4: Adjust for your shortcomings
• 21:16 Lesson 5: Let go of expectations & celebrate small wins
• 25:32 Closing thoughts + invitation to my live class

Links mentioned on this episode

Register for my free class: https://sidehustlepro.lpages.co/your-first-1000-downloads/

Click here to subscribe via RSS feed (non-iTunes feed): http://sidehustlepro.libsyn.com/rss

If you’re looking for a community of supportive side hustlers who are all working to take our businesses to the next level, join us here: http://sidehustlepro.co/facebook

Side Hustle Pro – @sidehustlepro

#SideHustlePro

Hosted on Acast. See acast.com/privacy for more information.