Know Pain, Know Gain

Latest Episodes:

100: 100 Episodes and Beyond Jun 15, 2020

Show notes

“Helping other people do what I did without having the painful experience that I had is what I wanted for others, to both help them understand themselves and get to the business side of things right.” -Jay Rooke

Know Pain Know Gain is at 100!

Another milestone has been added to our journey together and this is because of your loyal support and unending encouragement. No podcast, no show, no endeavour would have any success by itself. THANK YOU VERY MUCH for tuning in weekly to Know Pain Know Gain-Entrepreneurship Made Real!

A big THANK YOU also to Podcast Magazine for naming this podcast, “Editor’s Pick”.

Stay tuned as we move forward together to 100 episodes and beyond.

Look forward to more great and authentic entrepreneur stories to move past all the unnecessary pain in your journey and head straight to making a career path that brings you success and satisfaction.

Jay has been interviewing a number of business geniuses for the past 99 episodes. But who is this man behind the mic? Today, Jay sits as his own guest in his own show. Don’t miss out on this special treat!

In this episode, Lisa Cherney, Founder of the Get F*cking Real Podcast interviews our very own KPKG host, Jay Rooke. Jay and Lisa discuss: Jay’s life in various roles- as an attorney, as a chef, as an entrepreneur, and as a coach and the lessons learned in decision-making, engaging in personal development, transitioning from corporate to entrepreneurship, finding clarity when everything starts to fail, revitalizing strength despite overwhelming emotional agony, getting out of survival mode, finding a career that align with your higher self, internalizing and harmonizing every aspect of your life, and so much more…

Visit https://jayrooke.com/100-Lisa-Cherney-Interviews-Jay-Rooke/ for resources and show notes.

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Episode Highlights:

00:00:25 Tables Turned

00:02:36 Jay Behind The Mic

00:11:40 The Big Decision

00:24:10 Fortunately Unfortunate and Back To Corporate

00:31:49 Jay’s Personal Development Journey

00:40:16 Survival Mode To Further Down The Spiral

00:49:22 Grandma’s Message

00:56:46 Death and Rebirth

01:05:50 Internalize and Harmonize

01:10:36 Entrepreneurship and Self-fulfillment

01:15:40 Go On A JayWalk

099: Direct Your Own Evolution With Agility and Balance with Scott Jeffrey Miller Apr 14, 2020

Show notes

“Know when to be efficient and know when to be effective.” -Scott Jeffrey Miller

In this episode, Jay talks to Scott Jeffrey Miller, the Executive Vice President of Thought Leadership at Franklin Covey and author of the book, Management Mess to Leadership Success. Jay and Scott discuss: the difference of being reckless vs fearless, being emotionally agile, being a contingency planner, how to avoid disruptions, how to be emergent rather than deliberate, the importance of picking the right counselors, the visionary versus the integrator role, matching your ideas to your capacity to execute, what makes a successful CEO, staying on the top of creating contents, and so much more…

Visit https://jayrooke.com/099-Scott-Jeffrey-Miller/ for resources and show notes.

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Episode Highlights:

02:25 The Role of Thought Leadership

08:20 Be Emotionally Agile

13:16 Emergent vs Deliberate

21:44 Pick Your Counselors

28:33 Visionary vs Integrator- Who To Become

33:45 Your Job As The Leader

40:49 A Different Kind of Leadership Books

45:15 Top The Writing Game

098: Win at the Inside Game of Entrepreneurship with Amanda H. Young Mar 24, 2020

Show notes

“There is no ‘how’; you just do.” -Amanda Young

In this episode, Jay talks to Amanda Young, a Mindset Coach, Bestselling Author, Speaker, and Energy Healer. Jay and Amanda discuss: the necessity of a mindset shift, creating a filter for the information we receive, the importance of being fun and creative, dealing with your resentment of the corporate world, finding your alignment, being both human and spiritual in the business, the moral compass in decision-making, trusting yourself as opposed to deluding yourself, and so much more…

Visit https://jayrooke.com/098-Amanda-Young/ for resources and show notes.

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Episode Highlights:

02:50 Why Personal Journey Is Important to Entrepreneurship

09:40 Create a Filter

15:33 Be Fun, Creative and Grateful! It’s How You Run A Successful Business

23:26 The Human Side of Entrepreneurship

30:18 The Spiritual Side of Entrepreneurship

34:31 The F Barometer: Family, Fun, Finance

41:40 The Moral Compass of Decision-Making

44:07 Trusting Yourself vs. Deluding Yourself

097: How to Navigate Through Tough Conversations with Integrity with David Wood Mar 03, 2020

Show notes

“To not say anything is out of integrity.” -David Wood

In this episode, Jay talks to David Wood, CEO at Tough Conversations International and Play For Real, High-Performance Coach, Expert on tough conversations, and Author of Get Paid For Who You Are. Jay and David discuss: how to artfully navigate through tough conversations, speak your truth, discern things out of your values, deal with integrity leaks with kindness, be transparent, and so much more...

Visit https://jayrooke.com/097-David-Wood/ for resources and show notes.

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Episode Highlights:

02:18 Day-to-Day Tough Conversations

08:12 What Does Integrity Mean For You

17:50 What Are Tough Conversations

23:08 Pay Now or Pay Later

26:22 What’s Considered As A Nitpick

29:39 Create An Impact When You Speak Up

39:19 Be Transparent

096: Capture More Than Your Customer’s Data; Earn Their Loyalty with Tom Coburn Feb 18, 2020

Show notes

“It's not just what you know about customers, but it's often how you know.” -Tom Coburn

In this episode, Jay talks to Tom Coburn, co-founder of Jebbit, a Boston-based startup that Tom created as a sophomore in college in a business competition. Tom later dropped out of college to pursue the business, and it's still growing 7 years later. Jay and Tom discuss: how to capture customer data through an interactive experience, changing how customers connect with your web site, how old is new, following one's heart, trusting the leap, beginner's mind, and so much more...

Visit https://jayrooke.com/096-Tom-Coburn/ for resources and show notes.

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Episode Highlights:

00:55 From Dorm Room to an Interactive Platform

04:23 How to be Sophisticated in Value Exchange

09:26 Earn Your Customer’s Loyalty

19:33 Experience Makes A Difference

24:30 Questions Worth Answering

31:00 Perfection Leads to Failure

36:39 Keeping the Balance

40:10 Avoid Inertia Drift and Focus on Developing Trust

095: Close the Gaps For Greater Brand Alignment with Rebecca Horan Feb 11, 2020

Show notes

“You don't necessarily have to be as overt about it but it's really important that you as the brand, understand what those values are so that you can make sure that everything flows out of them in alignment.” -Rebecca Horan

In this episode, Jay talks with Rebecca Horan, founder of Plot Twist, a Brand Strategy Consulting firm. Rebecca works with an array of business owners on nailing their branding and messaging to that it is authentic and emotive. Jay and Rebecca discuss: how good branding is all about consistency, storytelling in branding, feeling vs. thinking your brand, getting market feedback, strategically investing in your brand, how to pivot your brand and so much more.

Visit https://jayrooke.com/095-Rebecca-Horan/ for resources and show notes.

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Episode Highlights:

02:07 Loving the Brand

09:37 Branding and Consistency

17:30 The Meeting Point

23:15 How to Niche Down

29:38 Pay Attention to the Competition

31:39 Weave Your Values Into Your Brand and Reinforce

42:57 Unleash Your Great Skills

46:44 Weave Your Story Into Your Brand

094: The Intersection of Love and Entrepreneurship with Theora Moench Feb 04, 2020

Show notes

“Investing your time, money and energy is the only way that you create transformative results in any area of your life.” -Theora Moench

In this episode, Jay learns from Theora Moench, a love and relationship expert who shares her insights about the intersection of love and entrepreneurship. All entrepreneurs need more love, so here are some of the things they talked about: when it comes to love, little changes yield big results, how to get as good at love as you are at business, entrepreneurship, and relationships as vehicles for personal growth, how to create healthy relationships during stressful times, how time fixes nothing, and so much more...

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Episode Highlights:

02:24 Missing the Relationship Norm

06:46 What Is Love?- Not Your Typical Definition

14:22 The Difference Between Business and Love

22:22 The ROIs of Love

26:54 Entrepreneurial Emotional States

28:10 Go From Work Mode to Connection

35:28 Se Up Reasonable Expectations on Your Relationship

40:21 The Right Timing

45:36 Wise Spending For a Happier Relationship

093: Amplify Your Platform By Business Automation and Making the Right Connection with Steve Gordon Jan 28, 2020

Show notes

“A really great referral system is… all that a business will ever need if they execute it.” -Steve Gordon

In this episode, Jay interviews author, podcast host and founder of The Unstoppable CEO, Steve Gordon. Steve has made the transition from becoming a CEO of an engineering firm (at age 25!), to launching his current brand, where he helps service-based entrepreneurs increase their visibility and authority so they can increase sales. Jay and Steve discuss: how to break revenue plateaus, mastering minimalism before you expand, referral strategies (Steve's written a book on the topic!), patience in running one's business, ROI on investing in advisory services, podcasting as a growth medium, and so much more...

Visit https://jayrooke.com/093-Steve-Gordon/ for resources and show notes.

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Episode Highlights:

02:03 Building Marketing Systems

07:00 Business Symptoms

14:45 The Attention Ladder

23:03 Unstoppable CEO

31:15 ROI in Taking Advantage of Advisory Services

41:40 Podcasting As A Growth Medium

46:13 Balance Your Role As Podcast Host And Guest

50:17 Get Free and Helpful Resources

092: Use Legal To Grow Your Business with Victoria Smolyar Jan 21, 2020

Show notes

“You have to approach the law just like you approach any other aspects of your business… from a position of power and not from a position of fear.” -Victoria Smolyar

In this episode, Jay chats with Victoria Smolyar, a business attorney that runs a virtual law firm in New York City. The two discuss legal challenges for small business owners and early-stage entrepreneurs, how business owners can change their viewpoint of working with a business attorney, ostrich syndrome, embracing being woo-woo, leveraging the law for growth and much more....

Visit https://jayrooke.com/092-Victoria-Smolyar/ for resources and show notes.

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Episode Highlights:

01:49 From Music to Business to Law

06:04 How Early Stage Entrepreneurs Should Think About Working With An Attorney

18:16 Approach Legal Matters with Power

25:13 Know Your Stuff

34:47 Common Mistakes Early Stage Entrepreneurs Make

38:07 Shift From Corporate Mentality

43:20 Not Your Typical Lawyer

47:21 Keep Your Motivation Burning

091: Business Essentials in Human Innovation with Stephan Thieringer Jan 14, 2020

Show notes

“...everybody has inherently great qualities.” -Stephan Thieringer

In this episode, Jay talks with Stephan Thieringer, the founder of Human Innovation Garage in Boston. Stephan is a brilliant strategist who understands that the inner-game of business is where the battle is lost or won. Jay and Stephan discuss: business empathy, learning how to fail, fitting in mindset versus contributing mindset, entrepreneurial agility/finesse/grace and diversifying your sources of advisors.

Visit https://jayrooke.com/091-Stephan-Thieringer/ for resources and show notes.

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Episode Highlights:

02:32 The Human Innovation Garage Cores

05:07 Open Dialogue, Vulnerability and Empathy in Business

12:07 Leadership Laid Out

23:57 Do Not Underestimate Millennials

28:26 Perfectionism- the Destroyer of Culture and Teams

32:58 Agility in Human Innovation