“I want self-managed people, especially for Halocracy. It's a self-managing environment, that needs people that are capable of individual self-management to be part of a team that is self-managing.”

— Brian Robertson

On this week's episode, Sachit (@sachitgupta) sits down with Brian Robertson (@h1brian) to discuss a management framework designed to get things done using a system of agile, self-organizing networks.

Brian is an entrepreneur, organization-builder, recovering CEO, and the Pioneer of Holacracy - an exciting and revolutionary management philosophy that turns everyone into a leader. The philosophy distributes authority and decision-making throughout an organization, and defines people not by hierarchy and titles, but by roles.

Tune in to hear Brian explain how the Holacracy method can help you create structures and ways of making decisions that empower everyone in the organization. Make sure you have your notebooks ready because this one's a cracker!

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Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

(00:00) - Introduction
(02:03) - The main idea behind Holacracy
(06:50) - How Brian discovered and built Holacracy 
(08:41) - To create clarity, ask these essential questions 
(11:30) - The one thing people misunderstand about Holacracy
(13:13) - The modern management hierarchy
(17:04) - Where to start when implementing Holacracy
(20:08) - Power and ownership under a Holacracy
(23:17) - How to distribute power throughout an organization
(25:45) - Support and mentorship in a Holacracy
(28:35) - Imagine having the best firing system in the world
(34:15) - Key steps to ensure you’re hiring the right people
(37:18) - Patterns that inform great hiring
(44:10) - Pitfalls to look out for when implementing Holacracy
(47:30) - How to avoid slipping back into old management habits
(50:19) - How long it takes from implementation to success with Holacracy
(57:10) - Ways Holacracy creates order, structure, and alignment in an organization
(01:01:02) - How to properly manage remote teams 
(01:03:04) - Tips for running better meetings
(01:07:05) - How Holacracy drives creativity in teams
(01:11:02) - The story of Medium and Zappos using Holacracy
(01:15:33) - The types of companies currently having success with Holacracy
(01:18:45) - Brian’s definition of a conscious creator
(01:19:57) - Parting thoughts

On this week's episode, Sachit (@sachitgupta) sits down with Regina Gerbeaux (@_rpgbx) to discuss how creative founders can find business operators, onboard them, and create action trackers that keep everyone on the team efficient and accountable.

Regina is the executive coach for top-tier CEOs, Operators, and Investors. She is best known for her work as an operator scaling companies in size and revenue using the Mochary Method. Regina is also an excited founder of a bootstrapped music business she started in college that hit $1M of annual recurring revenue by the time she was 20.

Tune in to hear Regina explain the primary role of a business operator, the resources they need to be successful, and how you can help them deal with the added stress of juggling multiple positions in the business.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

[00:00] Introduction

[01:11] Why creative founders need business operators

[04:58] You don't have a company if you don't have people

[08:12] How to find people who are an ideal fit for your culture

[11:33] Don't underestimate the importance of great onboarding

[17:39] Reasons you should never hire takers

[24:16] How the CEO's psychology defines a company's leadership and success

[30:00] Benefits of cultivating trust with your people

[32:45] Effective ways to stay grounded

[37:35] How much process is too much process?

[42:05] How to start building processes from scratch

[48:48] Finding your zone of genius

[53:42] What are the different stages of an operator?

[01:02:11] How to create an environment where your operators thrive

[01:06:55] Why investing in your operators makes for good business

[01:08:30] 30-60-90 day plan: How to onboard new operators with ease

[01:14:55] The dos and don'ts of giving feedback to new operators

[01:19:10] Understanding the journey of creators

[01:23:53] You need to learn to let go

[01:26:31] What Regina is most excited about going forward

[01:35:40] Parting thoughts

Links and Resources:

Regina's LinkedIn

Connect with Regina via Twitter

Coachingfounder.com

Give and Take: A Revolutionary Approach to Success by Adam M. Grant PhD

“You must succeed. This company cannot take care of its people, unless the company itself is succeeding. So you can't have bloat, you can't have dead-weight. You need everybody to be at the tip, top shape, tip, top form, really pushing like superstars do.”

— Faith Meyer

This week Sachit (@sachitgupta) chats with Matt Mochary (@mattmochary), CEO and Coach and Faith Meyer (@FaithKMeyer), certified Executive and CEO coach at Mochary Method — A company that provides the practical tools that a CEO needs to be an effective leader.

Matt is a CEO coach primarily dealing with heads of tech investment firms and companies on how to be exceptional leaders and build the best organizations possible. Faith, on the other hand, is a CEO & Executive Coach with Mochary Method and is passionate about helping people tap into their fullest potential.

The trio has an amazing discussion that goes all the way from coaching Sachit live, to deep dives on outstanding company cultures, leadership, team behaviors, and the importance of joy in a company. You won't want to miss this! 

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

[00:00] Introduction

[01:10] The benefits of having deep friendships with your clients

[03:55] How to create a healthy boundary with your coaching clients

[06:15] Live coaching session: Sachit's frustrating experience building the A-Team of podcast creation

[15:20] Creating a good culture that everybody wants to be a part of

[17:00] How to make your people feel good and inspired

[21:15] Great leaders show their people that they genuinely care 

[22:55] Examples of companies that have successfully built great cultures 

[28:00] Changing and upgrading your team's behavior

[34:25] How to create a culture of transparency from scratch

[39:20] Ways to create joy at work and spark a culture of happiness in your team

[45:30] Why every leader needs to conduct an energy audit

[52:52] Is it possible to train an EA to run your business?

[01:05:55] The two types of people in the world

[01:07:35] The art and science of coaching

[01:13:22] Matt and Faith share the thing about coaching that brings them joy

[01:19:50] What coaching is and what coaching is not

[01:22:45] Common coaching complains and how Faith handles them

[01:23:45] Understanding the delegation trajectory and how leadership evolves over time

[01:27:30] The main idea behind a growth spiral

[01:31:50] How businesses can act as a force for good

[01:34:00] Parting thoughts

Resources

Heard:  how to make people feel it (2 min)

Motivating your team (3 min)

Brainstorming written (2 min)

Loudest voice in the room (1 min)

Energy Audit (3 min)

CEO role (2 min)

Onboarding a new hire (3 min)

“If you want to be a conscious creator, part of what you need to do is become skillful in facilitating the dialogue between your conscious mind and your subconscious.”

— Charles M. Jones

This week Sachit (@sachitgupta) chats with Charles Jones (@adaptaboy). Charles began the research project that led to the Effectiveness Theory of Emotion in 1982 while pursuing an interdisciplinary degree at the intersection of Computer Science, Cultural Anthropology and Evolutionary Psychology at the University of Michigan. After graduating with a B.S., Charles continued the research project in his spare time for the next 35 years, studying with Fernando Flores (Ontological Coaching), Richard Strozzi Heckler (Somatic Leadership) and Marshall Rosenberg (Nonviolent Communication). In parallel, Charles had successful careers as a software engineer and organizational and leadership development consultant.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

0:00 - Introduction
02:10 - Why do you describe yourself as the Maverick Cognitive Psychologist?
07:10 - Looking back at your high school period, do you think you were suppressing your emotions?
17:40 - How do different emotions work?
30:17 - How to stop procrastinating and start working
36:22 - How does your body keep a score of your emotions?
1:03:25 - How do we cultivate emotional literacy amongst people?
1:10:45 - Stories of people who have changed by reading your book
1:14:20 - Fast five questions with Charles
1:26:25 - Closing Remarks

“You got to like people, and you gotta recruit the people you want to be around. And then treat them cool and make sure you like your partner. And then find someone who can do organizational things.”

— Michael Lovitch

This week Sachit (@sachitgupta) chats with Michael Lovitch (@michaelovitch) and Hollis Carter (@hollisc), co-founders of Baby Bathwater Institute — A community comprised of some of the world’s leading minds and entrepreneurs, with a focus on helping bootstrapped entrepreneurs navigate the crazy world of business ownership while having good times and making lifelong friendships.

Hollis Carter is a serial entrepreneur and avid skier. He started his entrepreneurial journey in the early 2000’s, founding multiple companies, including a SAAS company he built into a 7-figure virtual business in less than a year. In 2013, he became a founding investor in Utah’s Powder Mountain Ski Resort.

Michael Lovitch, MA is a former special education professional, over-educated grad student, and floundering tech sales guy who decided at the age of 34 to take the entrepreneurial path because nothing else was working. He started a publishing company in the psychology space that ended up being a 7-figure endeavor, then parlayed that into a physician-based nutritional supplement company (RealDose Nutrition) thatended up with annual revenues of $50 million dollars before he sold out his stake.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

00:00 Introduction
00:26 What is a successful community?
09:19 When did your events start turning into a community?
13:55 How do you encourage your community members to connect with each other?
17:21 The process by which people come into baby bathwater
21:41 Patterns in people from the same type of business
26:53 How to create a good experience for people
37:00 How to deal with people that take advantage of the community
43:17 How to get feedback from the members of the community
47:40 What you should be thinking about in order to build a successful community
53:56 How to agree in a moment of disagreement
55:54 The vetting process for the Baby Bathwater community
58:12 In the process of building the community, what have you learned about yourselves?
1:02:29 What does it mean to be a conscious creator?
1:07:21 Closing Remarks 

“Persuasion doesn't mean to manipulate. Intention is everything. If it isn't in the best interests of the person you're persuading, you probably shouldn't do it.”

— Dave Lakhani

This week Sachit (@sachitgupta) chats with Dave Lakhani, former Entrepreneur, Founder, C level executive and event producer. As a founder, Dave started more than a dozen successful companies. Several of the companies he led have been on the coveted Inc. 500 list. He successfully set new sales and marketing records at every company he was with. As a consultant, he worked with more than 500 companies to develop profitable growth strategies. As a professional speaker, he addressed more than 2 million people in the past 15 years, and his books have reached hundreds of thousands of people.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

02:53 - Three things that people want in life

08:25 - What makes Donald Trump a great influencer and persuader?

19:35 - How to read people and spot lies

32:45 - Practical tactics and hero’s journey

58:46 - Books recommendations

“Creators need to understand that the game being played around them is rigged. And basically, if they don't understand a different way to play this game, they will get sacrificed in the algorithm and burnout because the platforms doesn’t care.

— Sachit Gupta

Recently I was a guest on Creators Are Brands with Tom Boyd — Creator of @BonusFootage on TikTok and Instagram, creator strategist for billion dollar brands, and all around hilarious person. Highly recommend his podcast! In this episode we discuss content strategies, inventory, and 6-figure sponsorship deals. After re-listening to this podcast, I knew I had to share it here, with you.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

(0:00) - Introduction

(03:56) - What is Platforms Media? 

(06:00) - Who the first person that anyone should bring on in their team, is.

(09:14) - How to start playing the content game differently

(16:15) - How to apply the 3M Method to fine-tune your niche

(19:40) - Is there a blueprint for six-figure sponsorship deals?

(22:55) - Selling content inventory in advance

(32:10) - Selling content inventory for short-form content — Should you do it? 

(34:30) - How you can build a team & start monetizing your audience

(41:08) - How to cater to cold leads and inbound leads

(46:09) - Should you partner with influencer agencies?

(48:55) - What infrastructure have you built for recording & delivering the content?

(52:45) - Who the first person is that you should partner with for content distribution

(1:02:45) - Closing remarks

“If you have good people and the right person in the seat, they're going to have a better hit rate than you. Which, may be jarring to people who are like, “I'm really good at business.” Well, it turns out, you, with limited information and partial focus, is not better than somebody else.”

— Michael Girdley

This week Sachit (@sachitgupta) chats with Michael Girdley (@girdley), business entrepreneur and investor. Michael is Chairman and co-founder of Dura Software, the second-largest software company in San Antonio, Texas. His Holding Company includes a variety of businesses including Codeup, Effectual Ventures (a venture studio), Red Runner Coffee, Near (a talent platform), and others.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

(0:00) - Introduction
(02:15) - The difference between a CEO, an operator, and an idea guy
(03:30) - The transition from being an operating CEO to a holding company’s CEO
(08:47) - Describing the HoldCo model and why he switched to it
(13:46) - Advantages & disadvantages of the HoldCo structure Vs one company model
(21:08) - How he quick started the HoldCo model of operating
(26:45) - What he has learned about hiring and retaining top performers
(34:02) - The process of finding & hiring CEOs, with some examples
(39:20) - Tests or questions you ask a candidate to check if they’re a good fit
(46:52) - How do you separate yourself from being a HoldCo’s CEO from a company’s CEO?
(51:21) - The day-to-day differences between being an operating CEO Vs a HoldCo CEO
(53:43) - The moment when Michael realized he don't know everything
(57:12) - What the operations of HoldCo actually looks like
(1:04:57) - Some of the early mistakes in the HoldCo model and how to avoid them
(1:10:33) - Rapid fire questions with Girdley 
(1:17:35) - Closing remarks

“More than half of the people I talk to are burned out and that's why they want to sell. And if you're burned out, it's not too late because you can still sell the business, but it's not the optimal time.”

— Alexis Grant

This week Sachit (@sachitgupta) chats with Alexis Grant (@alexiskgrant) Founder & CEO of They Got Acquired — a media company that features acquisitions of online businesses and the founders behind them.

Previously, she was EVP of Content at The Penny Hoarder, a personal finance media brand, where she worked alongside the founder as the third employee to scale the company’s content operations. She also founded The Write Life, an online community for writers she sold in 2021.

Lexi began her career as a reporter at the Houston Chronicle and U.S. News & World Report, before growing a boutique content marketing agency, which was acquired by The Penny Hoarder in 2015. She lives with husband and two young kids in Harpers Ferry, WV.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

(02:49) - Experience and highlights from building content teams

(04:41) - How big the content side of Penny hoarder got

(05:24) - Is the company a media company?

(06:40) - Ways to monetize before advertising

(09:07) - Her fav content niches / companies that got acquired

(11:22) - Elements to think about when determining how to position or frame a media site — How to monetize or set up to sell 

(12:49) - Lessons from research she did on how media companies can be sold

(14:56) - How much a content site would sell for

(17:37) - What should creators do to monetize their audience and content, properly?

(20:28)  - How creators can sell their businesses

(22:23) - The process from buyers reaching out, to finally selling the company

(23:57) - At what point should you hire lawyers, agents and other people?

(26:13) - The most common mistakes everyone was making, in terms of selling their business

(28:34) - Things you should have in order before going down the path to sell

(34:32) - Is it possible to sell some of the pieces of business that are burning out the owners?

(39:01) - Other things creators should be thinking about during the process of selling the business

(40:10) - Will increasing revenue using services, increase the multiple?

(44:39) - How does one start building a team?

(46:59) - What Lexi’s team looks like

(49:04) - At scale version, what does the team look like?

(51:42) - What do editors do?

(53:29) - Principles creators should know about while building a team

(56:14) - Commonalities in great hires

(58:54) - Tips on training and managing creative talent

(1:00:28) - Things they have taken from writing, to podcasting

(1:02:46) - How much of an investment it takes to grow from good to great, in terms of podcasting and content

(1:03:08) - AI-generated content and where it’s going to go

(01:05:06) - Finding the voice for your writing and newsletter

(01:06:51) - Alexis’s three favorite creators

(01:08:29) - What it means to be a conscious creator

(01:09:09) - What she is most excited about in the next 5-10 years

“Figure out — What is the business that you want to run? What's the level of involvement that you want to have? Make sure that your business model matches your psychological desire for your involvement with the business.”

— Tim Geoffrion

This week Sachit (@sachitgupta) chats with Blake La Grange (@blakelagrange) and Tim Geoffrion (@this.walking.life).

Tim Geoffrion is an investor, consultant, and an executive leadership coach to small business leaders. Since starting his practice in 2020, Tim has partnered with the founders of over 20 start-ups to work through both the practical and interpersonal challenges of starting and scaling a new business. His work has included helping founders: determine initial equity splits, communicate more effectively with lawyers and bankers, mediate long standing conflicts, part ways with key employees, implement strategic planning processes, create long-term hiring plans, set-up financial tracking systems, negotiate license agreements, and prepare companies to sell themselves or raise venture capital funding.

Blake, graduated high school early (16), started a self study through music, theology, real estate, and business. He became a record producer for a decade, then built an online mixing and mastering business which pivoted into the premiere online education business in the music industry. He scaled that business to a point where he was able to sell it. Through that journey, launched other successful offers online using other peoples experiences and expertise. He now works as a "record label" in the company Kollege, by finding underground talent and applying lessons learned from the info-product world to help create offers that help creators get paid to do what they love.

Follow our host, Sachit Gupta on Twitter and sign up for the Creators Collective Newsletter.

Do you want to learn how to make a living as a creator? Check out the CreatorsMBA.

(0:00) - Introduction
(01:00) - Where was Blake, in terms of business, when he reached out to Tim?
(02:59) - Tim’s first thoughts when he saw Blake and his business
(07:55) - How can people perceive business fundamentals correctly?
(11:42) - How does Blake look at a business in hindsight?
(17:08) - What levers a creator should be looking at to grow exponentially later on
(19:36) - Why did Blake decide on sharing profits with his teammates?
(29:20) - How Tim looks at things from an IFS perspective
(34:51) - Decisions that entrepreneurs should make through a psychological lens
(44:30) - Context on the partnership between Tim and Blake
(51:06) - Things co-founders should do during a partnership and while integrating teams
(1:03:33) - Different elements one should consider before selling a business
(1:05:42) - Specific changes that Blake made when selling his business
(1:12:11) - Different ways people can make money as a creator
(1:14:58) - Is there an idealized business structure that is best to sell?
(1:22:06) - Did Blake feel off while letting go of his business?
(1:27:11) - Psychological changes one goes through while selling their business
(1:30:56) - How the process can be made easier for them
(1:33:25) - Blake’s experience of letting go of his business
(1:40:48) - The difference between income and wealth
(1:47:07) - Tim’s advice on where to invest money after selling the company
(1:48:43) - 5 Fast Questions with Tim and Blake