Sachit Gupta on How to Build a Million Dollar Content Business

How to Go From Startup to Scale: Lessons from Top Business Operator Regina Gerbeaux

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

Inventing the MOST EFFECTIVE Management System | Holacracy by Brian Robertson

“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

This week Sachit (@sachitgupta) chats with Brian Robertson (@h1brian), Co-founder of HalocracyOne — A company that integrates the collective wisdom of individuals throughout an organization and offers a toolset for each person to enact meaningful change at any level of work.

Brian is the world’s foremost expert on Holacracy, a revolutionary framework for self-managing organizations. After years as CEO of an award-winning software company, he co-founded HolacracyOne to share this innovative method with other organizations. The result is increased transparency, greater accountability, constant innovation, and agility across the company. Holacracy is used by over 1,000 companies today – in healthcare, insurance, banking, retail, technology, nonprofit and government sectors and in places as diverse as Dubai, Shanghai, Amsterdam, London, Berlin, New York, Bangalore, Las Vegas and rural Africa. Brian is thrilled to see this method take root and grow with such force.

Brian is the author of the book Holacracy: The New Management System for a Rapidly Changing World. He speaks at conferences, holds trainings, and consults for organizations across the globe.

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

02:25 - What does Brian do in Holacracy?

03:25 - Why is Holacracy better?

11:05 - While building a system, how can someone initiate from their first instinct?

15:00 - Where the concept of having a centralized structure came from

25:50 - Your vision for distributing power, even when not everyone is ready for it

28:35 - What does support and mentoring the people in your company look like?

33:27 - Who decides the roles in Holacracy?

37:35 - The hiring process within the company

45:05 - Great questions to ask when hiring someone

49:36 - Some of the common pitfalls you should watch out for

58:32 - Personal transformations that leaders go through

01:03:30 - Why companies without hierarchy perform better

01:07:19 - How to manage teams better

01:13:21 - How Holacracy helps in decentralized systems

01:22:15 - Some of the types of companies that are using Holacracy

01:25:30 - What being a conscious creator means to Brian

01:26:40 - Closing Remarks

Matt Mochary & Faith Meyer on Culture Building, Leadership and Growth

“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 coaches the heads of Silicon Valley tech investment firms and companies on how to be the best leaders and build the best organizations possible. His philosophy and method are captured in both Mochary Coaching Methodology (CEO) as well as his book The Great CEO Within (on Amazon, or online). Matt specializes in helping a CEO and company (or investment firm) transition from free-wheeling startup to dominant enterprise.

Faith is a certified CEO and Executive Coach with Mochary Method. She is a prior COO, CEO and VP, has over two decades of experience in leadership, building high performing teams, managing hundreds of direct reports, and scaling companies.

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

02:40 - How to prepare before you start coaching other people

05:35 - The boundaries between coaching & becoming friends with your clients

07:40 - How to create a strong culture 

25:55 - Examples of companies that have taken their advice on culture + how it created a ripple effect

31:20 - How to upgrade the behavior of your teammates

36:45 - How to create a culture of transparency and candor in a company

42:15 - How to go about creating a culture based on joy?

57:20 - Can a person actually be trained in a year and then run a business for you?

01:10:00 - How shadowing can help run great businesses

01:12:11 - How you can bring your own perspective into coaching curriculum 

01:17:50 - What aspects of coaching bring Faith and Matt joy?

01:24:10 - Some of the hard coaching sessions that Faith and Matt have had

01:26:30 - Some of the most common complaints + funny moments that they’ve had

01:28:22 - What you can do with your free time as a leader

01:32:20 - Growth spirals

01:35:00 - Why seeing a business as a force for good is so important 

01:38:45 - Closing Remarks

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)

Charles Jones — Cognitive Scientist on Stopping Procrastination, Stress & How Emotions Work

“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

Michael Lovich and Hollis Carter on Building a 7 Figure Business from a Community

“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