Surviving the Side Hustle

Most of the decisions keeping you stuck do not matter nearly as much as you think. Jordan Meyer is the founder of Addie Health, an Austin based skincare brand built for the 30 million Americans on GLP-1 medications, and the former president of Obagi, where he led a hardcore turnaround through an SEC investigation, a near delisting, and 80 to 90 hour weeks. He walks Rob through what that pressure taught him about focus, and how he now sorts decisions so the small ones stop eating his time.

The conversation covers why the top job comes with the most responsibility and the least direct control, the Ozempic face problem that inspired Addie Health, and why Jordan scrapped his med spa and dermatology plan to chase pharmacy and telemedicine instead. Rob and Jordan also get into building a network from scratch through conferences, why the best follow up is a text and a selfie, and three practical ways to get unstuck.

Topics Covered:

- What leading a public company turnaround felt like day to day, and why you have to work through the agency of others

- Why saying no to almost everything is the only way to execute well on what matters

- How GLP-1 medications age the skin and the gap in the market that became Addie Health

- Moving from med spas to pharmacies and telemedicine, closer to the moment of prescription

- Using conference stages, fast follow up, and introductions to build a network in a brand new space

- When to automate follow up and when to keep it one to one

- Segmenting decisions by how much capital and founder time they commit

- Time blocking the work you avoid, changing your environment, and protecting your sleep

Chapter Timestamps:

00:00 Show intro

01:38 Welcome and Jordan's background

02:50 Inside a hardcore turnaround

03:48 The most responsibility, the least control

05:31 Narrow your focus and say no

07:01 What Addie Health is building

08:11 The Ozempic face problem

09:45 Pivoting from med spas to pharmacy and telemedicine

11:40 Why speed is a startup's advantage

13:08 Building a network from zero

14:37 Conferences, follow up, and introductions

15:08 Systems versus a personal touch

17:37 Quick break

18:16 Stagnation and the what ifs

19:25 Segmenting your decisions

21:01 Time blocking the work you avoid

21:56 Change your environment

23:43 Why sleep drives better decisions

24:51 Where Addie Health is focused now

26:37 Where to find Jordan

27:49 The through line of a career

29:57 Wrap up

Connect with Jordan Meyer:

Addie Health: https://addiehealth.co

LinkedIn: https://www.linkedin.com/in/jordanpmeyer/

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

Picture a room nobody wants to be in: grieving siblings who have not spoken in years, and a funeral director who has about three minutes to earn their trust. That was Jay Jacobson's classroom for 45 years. Jay is the founder of Jacobson Professional Staffing and the guy behind Jay's Cookies, and he now teaches the skills he built in those rooms to the next generation of leaders.

In this Friday recap I pull out what stuck with me from my conversation with Jay. Reading the room is a discipline you can train, not a talent you are born with. His real edge is observation before action: he walks in and starts seeing before he starts doing. That maps straight onto the Prime Performance process. Clarity means knowing what you are working with before you work on it. Influence comes from being tuned into the people in front of you, not from volume or authority. And his 49 pound health reset is the energy principle doing its work, because you cannot hold that kind of presence on fumes. I close with one thing to try this week: in one conversation, pause, observe, and then act.

Chapter Timestamps:

00:00 Show intro

01:39 A room nobody wants to be in

02:07 Jay's 45 year classroom

02:35 Two very different worlds

03:03 Lessons from a nine year old paper boy

03:26 Four decades in funeral service and United Flight 232

03:47 Testifying before the Senate and turning it into a curriculum

04:17 The emotional weight of funeral service

04:38 Helping young professionals build balance early

05:04 When a hobby takes off fast

05:25 A 49 pound personal reset

05:47 Reading the room is a trainable skill

06:14 Observation before action

06:39 Prime Performance principle: Clarity

07:07 Prime Performance principle: Influence

07:28 Energy and how the principles feed each other

07:58 Jay's coaching and his book

08:22 Where to find Jay

08:32 Thank you, Jay

08:53 One thing to try this week

09:14 Follow the show

Connect with Jay Jacobson:

Jacobson Professional Staffing: https://jacobsonprostaff.com

Jay's Cookies: https://jayscookies.net

Listen to the full conversation with Jay Jacobson in E231.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

You have about three minutes to earn someone's trust, and in funeral service that is all you ever get. Jay Jacobson spent 45 years in funeral service, founded Jacobson Professional Staffing, runs the gourmet cookie company Jay's Cookies, and wrote Lead by Legendary Example. He walks Rob through what a lifetime of sitting with families on their hardest days taught him about leadership, trust, and playing the long game.

The conversation covers what Jay learned about people as a nine year old paper boy, why young professionals are losing the ability to read a room, and how a simple thank you tray for funeral homes grew into a cookie business shipping all over the country. Rob and Jay also get into how both businesses survived COVID, the 2 AM idea that rebuilt community for remote teams, and the 10 session team course built into the back of his book.

Topics Covered:

- Why the paper route taught Jay that people needed a visitor more than a newspaper

- How phones are replacing the years when we learn to read body language and tone

- The three minutes you get to build trust, and why open ended questions come first

- Rewarding employees for a satisfied customer instead of only a closed sale

- Thinking in generations instead of quarters, the long game of funeral service

- Sending thank you gifts on St. Patrick's Day instead of getting lost at Christmas

- Delivering cookies to remote employees on the same day to recreate community during COVID

- Being brutally honest but kind, and the 10 session leadership course in Lead by Legendary Example

Chapter Timestamps:

00:00 Show intro

01:39 Welcome and Jay's background

03:37 Leadership lessons from a nine year old paper boy

05:11 Why we are losing the ability to be present

07:13 The three minutes you have to earn trust

09:46 Paying people for the values you say you have

10:52 The generational long game of funeral service

12:15 How a thank you tray became Jay's Cookies

14:50 Send your gifts when nobody else does

16:25 Why tangible thank yous beat AI generated messages

17:16 Keeping two businesses standing through COVID

18:32 Recreating community with same day cookie deliveries

20:02 How COVID changed funerals for good

22:00 Quick break

22:37 Where the ideas come from: solving problems at 2 AM

25:37 Faith, family, and work balance in a high stress profession

26:42 The story behind Lead by Legendary Example

28:24 Brutally honest, done kindly

31:33 The 10 session team course inside the book

32:42 Where to find Jay

34:28 The one thing the next generation needs to learn

Connect with Jay Jacobson:

Jacobson Professional Staffing: https://jacobsonprostaff.com

Jay's Cookies: https://jayscookies.net

Lead by Legendary Example is on Amazon and Apple Books, in print and audio.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

"You have two choices when life knocks you flat. You can be a victim of your circumstances or you can be a victor." Anthony Guastella lived that choice for six years with Lyme disease, through joint pain, thyroid issues, and doctors telling him this was just his life now. He said no, went hunting for answers, and made himself a promise: when he got to the other side, he would do the same for other people. Today he is a health coach, podcaster, speaker, and writer behind Anthony Guastella Wellness. If you have ever felt stuck in your body, stuck in your head, or just stuck, this one is for you.

In this Friday recap I pull out what stuck with me most. Podcasts as the tool that taught him when nothing else could. The internal blocks that do not disappear even after you come through something hard, and the frustration of knowing exactly what you want but not getting there as fast as you want to. Why most people quit their podcast watching the numbers instead of holding on to the mission. His belief that your inner world creates your outer world. And his answer to people who confuse short term pleasure with fulfillment: fun is winning. I map it all to the Prime Performance process, especially resilience, intentionality, and why you have to get eyes on where your energy is draining before you can redirect it. Then I close on the one question I want you to sit with next time something goes sideways.

Chapter Timestamps:

00:00 Show intro

01:38 Two choices when life knocks you flat

02:02 Victim or victor

02:06 Meet Anthony Guastella

02:36 Six years with Lyme disease

02:57 Choosing the path of empowerment

03:21 A promise kept

03:41 The internal blocks do not just disappear

04:06 Consistency and holding on to the mission

04:35 Your inner world creates your outer world

05:01 Fun is winning

05:27 The mission is the reward

05:40 Resilience and intentionality

06:05 Energy is a currency

06:25 Get eyes on the drain

06:52 The work is always on the person first

07:08 Who Anthony is for

07:37 Thank you, Anthony

08:02 Am I being a victim or a victor?

Connect with Anthony Guastella:

Website: https://anthonyguastella.com

Podcast: Anthony Guastella Wellness, on your favorite podcast app

Listen to the full conversation with Anthony Guastella in E229.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

Six years of Lyme disease, joint pain, thyroid issues and fibromyalgia left Anthony Guastella with two choices: be a victim or be a victor. He chose victor, and the number one tool he used to find answers was podcasting. Today Anthony is the founder of Anthony Guastella Wellness, a certified health coach, speaker, podcaster and the writer of more than 350 articles, and he walks Rob through how taking 100 percent responsibility turned his pain into his purpose.

The conversation covers why your mission has to be bigger than your current circumstances, why consistency beats intensity, and why your inner world creates your outer world. Rob and Anthony also get into what inner work actually looks like day to day, Rob's story about playing rugby as "future Rob" instead of "college Rob," and why agency is the first thing Anthony wants every client to walk away with.

Topics Covered:

- Why it may not be your fault, but it is your responsibility

- Holding a long term mission over immediate gratification when nothing seems to be working

- How podcasting became Anthony's education and, later, his platform

- Doing one set instead of three and still giving yourself credit for showing up

- Consistency over intensity: keep the commitment, let the process adapt

- Giving yourself space to think and asking empowering questions instead of disempowering ones

- Overcoming yourself inside your circumstances, not the circumstances themselves

- Why disease does not happen overnight, and neither does health

Chapter Timestamps:

00:00 Show intro

01:38 Meet Anthony Guastella

02:53 Victim or victor: choosing 100 percent responsibility

04:45 Long term mission over immediate gratification

06:10 How podcasting became his education

07:09 Not your fault, but your responsibility

08:38 Turning pain into purpose

10:35 Reaching the masses and what coaching really is

12:00 Where consistency broke down

14:23 One set instead of three still counts

15:06 Consistency over intensity

16:49 Your inner world creates your outer world

18:09 What inner work looks like right now

20:32 Building capacity and a resilient nervous system

20:56 Quick break

21:33 Rob's rugby story: playing as future you

23:57 Put your energy where you have control

24:25 What clients walk away with

27:44 Disease does not happen overnight, and neither does health

29:08 350 articles and starting before you are ready

30:59 Where to find Anthony

Connect with Anthony Guastella:

Website: https://anthonyguastella.com

Podcast: Anthony Guastella Wellness, on your favorite podcast app

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

"I hold a lot of trauma in my throat." That is how Shakti Sharma described her starting point: a shy kid who wanted to stay in the corner and not be seen. Today she is a serial entrepreneur, a manifestation coach, and the founder of the Feminine Wealth Movement, where she helps women entrepreneurs, coaches, healers, and service providers turn a passion into a 100K offer sold directly to organizations. If you are sitting on a skill or a gift and telling yourself nobody will pay real money for it, this one is for you.

In this Friday recap I pull out what stuck with me most. The four years she built on the side while holding a full time job. The yoga studio launch where nobody came on Saturday, and the one person on Sunday who felt like gold. The outreach and marketing that used to freeze her completely, and why she had to heal herself while running a healing business. And her secret, inner state alignment paired with the outer structure of her Feminine Wealth Launch Framework. I map it all to the Prime Performance process, especially resilience, clarity, and opportunity, and why opportunity tends to show up right after clarity does. Then I close on the one idea I want you to sit with: the belief has to catch up with the business.

Chapter Timestamps:

00:00 Show intro

01:38 I hold a lot of trauma in my throat

02:02 Meet Shakti Sharma and the 100K offer

02:30 Welcome to the Friday recap

02:58 Four years building on the side

03:26 One person on Sunday felt like gold

03:53 Ten thousand dollar months and a second business

04:23 The outreach that used to freeze her

04:52 Healing yourself while running a business

05:20 Inner state alignment

05:47 The Feminine Wealth Launch Framework

06:15 Freedom and a juicier life

06:41 Resilience, clarity, and opportunity

07:09 Clarity is the foundation

07:37 Opportunity shows up after clarity

08:04 Who Shakti is for

08:30 Thank you, Shakti

08:57 The belief has to catch up with the business

Connect with Shakti Sharma:

Feminine Wealth Movement: https://femininewealthmovement.com

Listen to the full conversation with Shakti Sharma in E227.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

Nobody showed up to the opening of Shakti Sharma's first yoga studio. One person walked in a day or two later. Shakti spent 12 years in financial services, management consulting, and investment banking, then built an intuition practice on the side before making the leap. From that empty room she grew to consistent $10,000 months, expanded next door, bought a second studio, and watched the pandemic shut both. She rebuilt online, and her Feminine Wealth Movement is now a $600,000 plus business. She walks Rob through how listening to her heart, not another spreadsheet, became her strategy.

The conversation covers the quiet argument that sent her to a hotel room and opened her up to her intuition, why a side hustle is a rebirth and not just a paycheck, and the landlord who paid for her entire buildout. Rob and Shakti also get into her three pillars of energetic alignment, marketing, and sales, why your reputation sells before anyone hits your funnel, and the 100K Offer System she teaches.

Topics Covered:

- Checking every box in consulting and still feeling a void she could not name

- The inner voice that told her she had abandoned her heart to accomplish all of it

- Starting a side hustle helping women hear their intuition, and why side hustles are about more than money

- Why heart-centered relationships are the biggest marketing lever in a small business

- Outgrowing a room built for eight, and the landlord who paid for the buildout next door

- Losing both studios to the pandemic and choosing to own the story instead of playing the victim

- Her three pillars: energetic alignment, marketing that gets people to raise their hand, and selling one to many

- How the 100K Offer System helps practitioners sell to hospitals, school systems, and banks

Chapter Timestamps:

00:00 Show intro

01:39 Meet Shakti Sharma

03:34 Living the consulting dream and still asking what is next

06:08 The night that cracked everything open

10:15 You have abandoned your heart

11:38 How her intuition side hustle began

13:01 Rob on robot mode and the song that broke it open

14:34 Why a side hustle is a rebirth

18:06 Going full time and the launch nobody came to

19:25 Why heart-centered relationships beat any campaign

21:49 Outgrowing the room and the landlord who said yes

26:09 Deeper connections beat more connections

27:52 Quick break

28:28 A second studio, then the pandemic

32:35 Rebuilding online when everyone is screaming for attention

33:48 The three pillars: alignment, marketing, and sales

37:50 Marketing that gets people to raise their hand

41:40 Reputation is the part nobody talks about

42:59 Inside the 100K Offer System

46:13 Where to find Shakti

Connect with Shakti Sharma:

Free community and trainings: https://femininewealthmovement.com

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

What if the thing keeping you stuck is not a lack of hustle but a lack of permission? This week I am unpacking my conversation with Jeremy Shapiro, founder of Your Business Growth Playbook and a serial entrepreneur who has spent three decades in the trenches with seven, eight, and nine figure founders who hit a plateau and cannot figure out why what got them here will not get them there. Jeremy has lived abroad with his family, gone fully offline when his kids were born, and traveled entire summers without the business falling apart, and it all traces back to a quiet line he drew at a dinner table.

In this Friday recap I pull out what stuck with me most. The date night phone buzz that showed him how half present he had become. The ant trail image behind how his repeatable playbook finally revealed itself. The mountain biker client he freed with a single part time hire. And the idea I keep coming back to, that the secret is not hustle, it is permission, the permission you give others to reach you and the permission you give yourself to be a human being with limits. I map all of it to the Prime Performance process, especially energy and intentionality and the clarity that only shows up once you stop living one buzz away from reactive mode. Then I close on Jeremy's challenge to define success on your own terms instead of chasing somebody else's finish line.

Chapter Timestamps:

00:00 Show intro

01:38 The dinner table phone buzz

02:07 Meet Jeremy Shapiro

02:37 Build something real without losing everything

03:02 The ant trail and the hidden playbook

03:30 How the repeatable formula emerged

03:58 Seeing his own system too late

04:26 The date night story every founder feels

04:51 The slow bleed of presence

05:18 Performance runs on the boundaries you enforce

05:46 One hire and the real secret, permission

06:15 The permission you give yourself

06:35 Energy, intentionality, and clarity

07:04 You cannot optimize what you have not faced

07:31 Who the book was written for

07:59 The Profit Blueprint program

08:27 Define success on your own terms

09:00 What does made it actually look like for you

Connect with Jeremy Shapiro:

Book and Profit Blueprint program: https://yourbusinessgrowthplaybook.com

LinkedIn: https://www.linkedin.com/in/jeremyshapiro/

Your Business Growth Playbook is also on Amazon and Audible.

Listen to the full conversation with Jeremy Shapiro in E225.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

Can you build something real without it costing you everything else? Jeremy Shapiro has spent 30 years answering yes. A serial entrepreneur and the author of Your Business Growth Playbook, Jeremy has built companies that let him live abroad, unplug for three months at a time when each of his kids was born, and travel entire summers without the whole thing falling apart. He walks Rob through exactly how he engineered a business that keeps running and growing while he steps away.

The conversation covers the dinner table moment that made Jeremy set his first hard boundary with clients, why hustle only gets you off the ground, the "ant trail" idea behind his growth playbook, the pre-sell tactics he used to fund a course before building it, and the different walls that six, seven, eight, and nine figure founders hit.

Chapter Timestamps:
00:00 Show intro
01:38 Meet Jeremy Shapiro and 30 years of serving entrepreneurs
02:55 The first date phone buzz that changed how he worked
03:20 The boundary his clients came to respect
05:06 Give people 24/7 access and they will take it
06:41 The mountain biking client who was burning out
08:12 How helping other founders became his lane
10:06 The ant trail and finding the hidden playbook
11:45 Perfectionism versus shipping the MVP
12:52 Getting real customer feedback before you build
14:16 Pre-selling a course before it existed
17:21 Ten months to publish the book the right way
19:07 The stages of growth from six to nine figures
20:19 Why the wrong-size advice can wreck your business
22:50 Quick break
24:01 Unplugging for three months when his kids were born
27:23 The demolition client whose accident forced systems
30:15 From self-employed to true business owner
31:01 Inside Your Business Growth Playbook
32:34 What is next and the Profit Blueprint program
34:24 The one belief he wants every founder to leave with

Connect with Jeremy Shapiro:
Book and free first chapter: https://yourbusinessgrowthplaybook.com
LinkedIn: https://www.linkedin.com/in/jeremyshapiro
Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.

Passion done with consistency and integrity over a long enough timeline becomes a legacy. That one line from Erica Christ has been sitting with me all week. Erica is a registered dietitian, a diabetes educator, and a classically trained Pilates instructor who has spent twenty years building FMR Wellness in Greenwich, Connecticut, one private session, one client, one word of mouth referral at a time. No franchise, no group classes, no trendy rebrand every couple of years, just conviction and repetition. And now she is bringing her daughter Julia into the business and building a succession plan that is every bit as intentional as everything else she has ever done.

In this Friday recap I pull out what stuck with me from our full conversation and how it maps to the Prime Performance process. I get into why Erica taught the why before the what with every single client, why the depth of her understanding is what actually kept people coming back and sending their friends, the quiet tension of wanting Julia in the business her whole life while genuinely letting Julia make her own choice, and how all of it connects to three ideas I keep circling back to: clarity as your protection against every shiny trend (Prime Principle 3), resilience reframed as staying the same through twenty years of an industry that kept changing around you (Prime Principle 1), and taking inventory before you take action.

Chapter Timestamps:

00:00 Show intro

01:38 Passion plus consistency becomes legacy

02:03 Meet Erica Christ, twenty years one client at a time

02:18 No franchise, no trends, just a succession plan

02:47 Finding Pilates through her own injury

03:27 Not about making money, about not losing money

03:54 Word of mouth and Julia earning her certification

04:20 The invisible hard parts nobody sees

04:49 The fear that classical Pilates could disappear

04:59 Wanting Julia in versus letting her choose

05:27 Her secret, teach the why before the what

05:42 Curiosity first, program second

06:41 Awareness is the whole product

06:50 Prime Principle 3, clarity as a trend repellent

07:20 Prime Principle 1, resilience as staying the same

07:44 Take inventory before you take action

08:24 Where to find FMR Wellness

09:18 What are you building, and is it worth passing down

Connect with Erica and Julia Christ:

Website: https://fmrwell.com

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

LinkedIn: https://www.linkedin.com/in/erica-christ-rd

Listen to the full conversation with Erica and Julia in E223.

Follow Surviving the Side Hustle at https://survivingthesidehustle.com for every episode.