Know Pain, Know Gain

Episode Highlights:

02:51 Content in the Business Context

05:48 Processes are Essentials

12:34 Going All-In

24:20 Single Parenting and Entrepreneurship

33:57 Scarcity Mindset No More

36:30 Riding the Emotional Roller Coaster

40:40 Prove It Before You Post It

46:37 Leadership and Number Failures

53:04 Failures as Milestones

089: Take the Entrepreneurial Leap the Healthy Way with Kevin McArdle Dec 31, 2019

Show notes

“If the only thing in your life is your business, there's a tendency to want to work on it all the time which is not necessarily the most healthy thing in the world.” -Kevin McArdle

In this episode, Jay connects with Kevin McArdle, founder of SureSwift Capital.

Kevin's company buys bootstrapped, successful SaaS businesses and then manages them as a holding company. They usually buy companies from software developers that are working on their business as a side hustle. Some interview topics include: stripping down your business model to core functions, ignoring the haters, high-stakes entrepreneurial leaps, aligning with one's niche, don't overcomplicate your business, navigating culture change, managing a remote work force, and so much more.

Visit https://jayrooke.com/089-Kevin-McArdle/ for resources and show notes.

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Episode Highlights:

02:08 How SureSwift Capital Move

11:35 Why People Sell Their Biz

17:11 Taking The Leap

23:24 Niche Down and Never Declare Victory

28:32 How Couples Can Become a Good Team

31:58 What’s Important When Nobody Cares

38:40 The Distinguishing Factor of a Holding Company

42:50 Navigating Culture Change

088: Effectuate a Culture of Trust as the Foundation for Your Business with Judy Foley Dec 24, 2019

Show notes

“If trust is not there, then no one will ever get the results that they're going to need.” -Judy Foley

In this episode, Jay talks with Judy Foley, author of Retaliation at the Highest Level and founder of The Culture of Trust. Judy focuses on cultivating and changing organizational culture, so this episode dials in on: being deliberate about culture creation early on in a business's growth cycle, upleveling and growing the business, "as is" versus "should be" mentality, increasing employee buy-in and engagement, trust as a growth multiplier, and taking calculated risks in your business.

Visit https://jayrooke.com/088-Judy-Foley/ for resources and show notes.

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Episode Highlights:

01:38 The Culture of Trust

07:08 Setting the Culture at the Forefront

15:31 The Role of EQ

19:44 Scalability vs Giving Honor

24:54 Do You Have Culture Issues?

28:00 Increasing Employee Buy-in and Engagement

37:42 Retaliation

41:00 Building Up the Trust

087: How to Succeed in Your Transition with Kelly Wilson Dec 17, 2019

Show notes

“It's good customer service to show your customers that you care enough to give them a quality professional product.” -Kelly Wilson

In this episode, Jay chats with Kelly Wilson, who has been running a voice over business as a side hustle for several years, and just left corporate to go all-in and make it her primary income. Jay and Kelly discuss: how to plan for success when going from side hustle to business launch, saying no to bad clients, how to find your magic, the terrifying experience of going all-in, exercising extraordinary focus while engaging the creative, and so much more....

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Episode Highlights:

02:18 Voice Over Calls Over

07:37 Get a Coach

09:44 Running the Side Hustle

21:54 How to Get Premium Pricing From VO

27:20 Are You Giving Quality Professional Product

32:47 Focus on ONE

41:57 Solidify Your Foundation

086: The Secret of Successful Entrepreneurs- Empathy in Action with Maria Ross Dec 10, 2019

Show notes

“We need more empathy, but we need to put empathy into action.” -Maria Ross

In this episode, Jay brings on author and founder, Maria Ross for an eye-opening dialogue around harnessing the power of empathy in the workplace. Maria is the owner of a brand consultancy, and recently published the book, The Empathy Edge. Jay and Maria discuss: entrepreneurial timing, not parking your values at the door, the business case for empathy and its connection to innovation and sales, curiosity in business, "it's just business", getting triggered, situational fluency and so much more....

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Episode Highlights:

02:30 Empathy in the Business Context

09:39 How Empathy Boosts Innovation and Productivity

15:00 Empathy and Decisiveness

19:47 The Practical Applications of Empathy

23:50 Empathy and Curiosity

27:09 The Science of Empathy Work Out

34:35 Empathy for Solopreneurs

45:04 Empathy and Hiring

085: Be “The Agent” of Your Entrepreneurial Journey- Scale Your Business Creatively with Christopher O'Donnell Dec 03, 2019

Show notes

“The more room you have to fail, the more space you have to innovate.” -Christopher O’Donnell

In this episode, Jay interviews Christopher O'Donnell, SVP of Product at Hubspot, and founder of the rock band The Providers. Christopher manages a rapidly growing creative team at Hubspot, and thus he and Jay chat deeply about fostering creativity as a small business owner, but also: adaptability as an entrepreneurial skill set, celebrating the little wins, soliciting feedback from the right people, imposter syndrome, gap awareness, running controlled experiments and viewing one's self as a talent agent/coach.

Visit https://jayrooke.com/085-Christopher-ODonnel/ for resources and show notes.

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Episode Highlights:

02:07 Shifting the Power in Shop & Buy

07:11 Implementing Peer Leadership

16:19 Be “The Agent”

24:26 Shaping Behavioral Styles Creatively

30:06 Celebrate

36:00 Simplify It Down

42:13 How to Make a Record

48:43 Your Dog Walking Time

084: Beat the Burnout Holistically with Sarah Argenal Nov 26, 2019

Show notes

“As we get to be more in control of our own lives, we feel differently in terms of how burned out we are or how balanced and happy we are.” -Sarah Argenal

In this episode, Jay chats with Sarah Argenal, founder of the Argenal Institute. Sarah is a speaker/author/coach that specializes in dealing with burnout, which is rampant in the entrepreneurial community. Jay and Sarah discuss identifying the symptoms of burnout, learning how one gets burned out, what to do about it if you are, and how we, as a culture, became so burned out so fast and how to leverage self-awareness to avoid burn out.

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Episode Highlights:

02:14 A Must Talk- The Burnout Hitch

06:45 Burnout Markers (the High Achiever and the Overachiever)

10:47 Where Burnout Starts- Your Choices

18:20 Beneath the “Overwhelmed”

22:31 Stop Reducing Yourself

27:58 Beat the Burnout Holistically

40:12 Know How To Live A Life that Really Works for You

46:55 The Humanity Wrestling Against Burnout

083: How to Spot a Good Mastermind Investment with Sara Christensen Nov 19, 2019

Show notes

“Doing this whole entrepreneurial, personal development journey by yourself is hard. It's really really hard and it's unnecessary.”

In this episode, Jay chats with the master of masterminds, Sara Christensen, founder of Kickass Masterminds. Jay and Sara have a candid conversation about the predatory nature of marketing "gurus," the isolation of entrepreneurship, how to find the right mastermind fit for you and your business, using "borrowed beliefs," the art of masterminding, and accelerating success through group dynamics versus the lone wolf mentality.

Visit https://jayrooke.com/083-Sara-Christensen/ for resources and show notes.

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Episode Highlights:

03:24 What is a Mastermind

09:08 How to Get the Right People Together

14:18 Curation and the Common Mistakes

18:50 Factors to Consider in Mastermind Investment

23:28 When to Join a Mastermind

28:25 Borrowed Belief

35:38 Evaluating A Mastermind

45:56 The “Time” Issue Rebuttal

082: Be a Highly Priced Entrepreneur as a LinkedIn Expert with Helen Pritchard Nov 12, 2019

Show notes

“Just pick something and go for it; and go for it really, really hard.” -Helen Pritchard

In this episode, Jay talks with Helen Pritchard, a LinkedIn expert who helps clients increase inbound lead generation. Brace yourself--Helen is not afraid to swear in delivering her message as she shares insights with us such as: why you should never ask for feedback, that you want to repel as many people as possible with your messaging, writing love letters to your prospective clients and how she grew her business as a stressed out single mom.

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Episode Highlights:

01:54 LinkedIn- A Cash Machine

05:41 4 Pillars of Content

14:26 Repel as Many People as Possible

23:16 Rule of 10

29:54 A Love Letter to Clients

36:30 Inbound Lead Generation

45:51 Be A Highly Priced Entrepreneur

51:12 Focus on the Next 300 Yards

081: Have Enduring Results for Relatively Limited Inputs with Dennis Kiley Nov 05, 2019

Show notes

“It's really important that we have that growth and expand the canopy and generate revenue and profit and keep expanding. But on the other hand, to bear in mind that if we don't also nurture those roots, that tree becomes really fragile when they start to blow.” -Dennis Kiley

In this episode, Jay interviews Dennis Kiley, founder of the Ecopsychology Initiative in Maine. Dennis has developed a training series that helps business owners understand and repair their businesses through the medium of the principles of nature. As such, the two discuss the value of nature in keeping the entrepreneurial mind calm, how to leverage nature to increase your problem solving ability, viewing your business as having seasons and acting accordingly, etc--it was a refreshing and out of the box dialogue with some immediately applicable takeaways. Check it out!

Visit https://jayrooke.com/081-Dennis-Kiley/ for resources and show notes.

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