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Reflections of a CEO

Reflections of a CEO

By Anthony Tumbiolo

A podcast highlighting the introspections of Jakt's CEO Anthony Tumbiolo. Reflecting upon the things that go on in a business that many do not see. From true feelings and emotions about the company to insights about what it means to be a CEO, this podcast has you covered.
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How To Build And Exit A Successful Business - A List Of Personal Reflections

Reflections of a CEOApr 29, 2020

How To Build And Exit A Successful Business - A List Of Personal Reflections

How To Build And Exit A Successful Business - A List Of Personal Reflections

I started Jakt, a digital product & innovation studio based in NYC back in 2012.

I built it entirely from scratch as its CEO into the $4M/year business that it is today.

And it’s definitely been a hell of a ride.

I’ve gone through the highest of highs and lowest of lows during all these seven years.

There were times I felt happy and fulfilled as I’ve ever been, just as times when I thought I couldn’t possibly sink any lower.

As of June of 2019 though, I’m no longer Jakt’s CEO.

The business was acquired by a much larger agency who also offered me a spot in its board of directors.

I’m moving onto a new stage in life and I couldn’t be more excited for what’s to come.

In today’s episode, I’m actually a guest in a friend’s Podcast.

He invited me to come over to share my story, learnings, and personal reflections from building a business with a virtual room of people.

Here’s what we touched on:

- The moment that spurred me to follow entrepreneurship (6:10)

- How my end-goal changed over time as I grew Jakt (10:50)

- When did I start noticing the company’s success (14:00)

- Should you invest in a sinking ship or fail quickly and pivot somewhere else? (18:00)

- Why sales are SO important (22:00)

- How did we approach our potential leads to generate new business and close them (30:00)

Apr 29, 202001:38:29
The Most Important Lesson I Learned From The First Time I Fired Someone

The Most Important Lesson I Learned From The First Time I Fired Someone

When I first started my agency Jakt back in 2012, I didn’t know what I was doing.

Sure, I could code and take care of the production work, but the business side of things?

I was figuring that out as it came.

NYU taught me about many things... but running a profitable agency wasn’t one of them.

And in 2015, I realized it didn’t prepare me to fire someone either.

To this day, I can admit it was one of the hardest things I’ve ever had to do.

I actually talked myself out of making the decision -- even when I believed it was the best for the business -- for a whopping SIX months before I finally sat down and took action.

If you’re struggling with that right now…

Or you’ve already fired someone, and you’d like to know another’s POV and experience...

This is for you.

I’ll touch on…

- Why I made the decision to let this employee go (3:03)

- The reasons why I talked myself out of it for so long (4:22)

- What helped me get through my mental barriers and stories to take action (7:42)

- The lesson I learned from that experience (13:10)

- Why you’re doing people a disservice if you don’t fire them quickly (13:49)

Apr 29, 202023:07
How Not To Die When Things Break: A Story Of When I Almost Closed Jakt

How Not To Die When Things Break: A Story Of When I Almost Closed Jakt

It was 2016. We had just closed at $2M in revenue last year, and I’m feeling great.

I couldn't know I would be considering shutting down Jakt a couple of months later.

Some of the events that unfolded that year almost broke me.

More than half of our team left us in a short period, clients were leaving us, I couldn’t seem to close any new business...

If you’re an entrepreneur, you might relate to this.

You might have hard times and think about shutting everything down because it’s not worth the stress, anxiety, or depression.

Reality is though: you’re not alone here.

Just as you, other people have been through their fair share of shit.

And if I got through mine, you can definitely get through yours.

In this podcast, I share with you the story of how I almost decided to shut down Jakt for good,

because I want to remind you that you’re not alone on this journey. And that things breaking might be a good thing for ONE special reason…

I’ll touch on:

- The TWO things that started happening within Jakt that almost broke me (3:38)

- Why things breaking turned out to be a blessing in disguise (8:12)

- How you need to frame these exact moments to actually grow from them (12:16)

Apr 29, 202019:19
How we grew from $1M to $4M in revenue

How we grew from $1M to $4M in revenue

For three years, my agency Jakt hovered around $1.5M to $2M in revenue.

From 2017 to 2018, we jumped from $1.7M to $4M. That’s a 134% increase.

How did we suddenly break through after a three-year dry spell?

You see…

There’s no silver bullet, just as there’s no “ONE thing” that I did to finally grow past the threshold we were stuck at.

It was the opposite in fact.

From changing the type of customer we serviced and the type of engagement we had with them…

… to varying the type of projects we accepted from short to long-term...

I realized Jakt couldn’t grow past the $2M if we kept things the same.

And in this podcast, I’ll be sharing with you the exact steps we took to do just that.

I’ll be touching on…

- The type of customer we first served at Jakt and why did we have low retention with them (2:03)

- What I realized was necessary to grow to $4M (5:05)

- Why our first customers didn’t want to bring our services in-house, and how this affected retention (6:04)

- How I changed the frame we set with new customers so we worked for more extended periods (7:50)

- Why offering services that were super important to their businesses - but not the main priority - helped us grow immensely (9:58)

Apr 29, 202018:13
The greatest lessons I’ve learned while running a $4M/year agency

The greatest lessons I’ve learned while running a $4M/year agency

Someone asked me two questions on Twitter the other day.

He said:

“Anthony, what’s the greatest lesson you’ve learned at Jakt?

And two - knowing what you know now, what would you have done differently?”

You see…

I don’t believe there’s “one greatest lesson.”

If anything, what I’ve learned throughout seven years while growing a multimillion-dollar agency is the opposite:

There are a TON of lessons, and I haven’t even yet scratched the surface.

Business wouldn't be a game with a constant amount of learning involved otherwise.

From the financial engineering principles I’ve used to stay profitable every single year…

… to creating a culture of high-performers and accountability at Jakt...

In this podcast, I’ll give you a rundown of a few lessons I’ve learned and what I’m doing differently moving forward.

Here’s what I’ll touch on:

- Why sales cures everything (5:25)

- Hiring an executive coach has a massive ROI (11:09)

- Look at your business as a machine comprised of various systems. Your job as the CEO is to design the machine (16:29)

- You are NOT that special (17:49)

- You are THAT special (18:32)

Apr 29, 202019:44
How do you scale your agency when things around you start breaking

How do you scale your agency when things around you start breaking

In the last episode of Reflections of a CEO, I covered the topic of the three big systems that every service-based business/agency has…

...and how you must make sure there isn’t an imbalance between the growth of each three.

Because if you don’t, your business might break.

This episode is meant to be a Part 2 of that topic, in where I go in-depth on what you should do as an agency owner when you feel that things start breaking.

This is a very important episode that, if you run an agency, will be helpful as you grow and scale your business.

I’ll touch on:

- Why you need to understand how an agency works to address the problem (2:12)

- Taking a step back and diagnosing the root cause of the problem(3:07)

- Why you need to look at your business and ask how can you replace yourself (3:52)

- How new agency owners might not have a 10,000-foot view of the systems, and what to do about it (7:18)

- What to REALLY expect from your employees as you grow (8:31)

- The difference between working ON the business VS IN the business (10:17)

- Why the News Business system is the last system you want to replace yourself from (12:24)

- Removing yourself too prematurely (13:48)

Apr 29, 202018:55
How To Balance The Three Systems That Make Up Your Agency

How To Balance The Three Systems That Make Up Your Agency

As you agency grows, stuff can start to break.

Over the years at Jakt and through the questions I’ve received from many other agency owners in our community, I realized why this happens.

It means you’ve reached the breaking point of the systems that worked for you before.

And they need adjusting.

In this episode, I’ll dive into the role each system plays in your business, how growth will cause an imbalance between them…

...and how you must constantly keep them evolving to not break.

I’ll also touch on:

- Why stuff starts to break in your agency as you grow (and why that’s okay) (1:06)

- The three main systems that compose your agency (2:13)

- The imbalance that falls on the systems as you grow (2:50)

- What you have to do to keep them from breaking (4:34)

- My experience with a Back-Office system that wasn’t evolving fast enough (7:04)

Apr 29, 202011:15
What should you do when you lose a big customer?

What should you do when you lose a big customer?

What do you do when you lose a big customer?

This is a question I was asked at, a community of agency owners I moderate who are looking to grow and build their business.

A member of the group recently lost an important client.

And they’re now in a kind of situation where they have to evaluate letting some people go or other alternatives like getting rid of their office space.

And I’ve been there, not just once, but multiple times in my career while running an agency.

If you run an agency, I hope this podcast helps you be more prepared if this ever happens to you.

I’ll touch on…

- My personal experiences with losing big customers (2:15)

- Why these are the moments when you get to see what you’re made of (3:31)

- Taking the time to process the loss (but not too much) - (5:03)

- Learning the lesson and adjusting (6:42)

Apr 29, 202012:22
How to know if you should take on an equity partner

How to know if you should take on an equity partner

Very recently, I got asked the question if I would ever bring an equity partner in Jakt, and why or why not would I bring someone onboard.

If it was the case I did, what would be the requirements or the situation needed to be?

Now, I’ve found out that looking for the right business partners is a lot like dating and trying to find the person you want to be with.

I had to go through several people to figure out what is important to me over the course of seven years.

And I want to share the lessons I’ve learned with you today.

I’ll touch on…

My first business partner at Jakt (1:05)

How finding business partners is a lot like finding the right person to date (2:43)

What breaks the partnership the majority of the time (4:24)

My personal requirements for business partnerships (6:30)

My good rule of thumb for evaluating potential partnerships (8:55)

How I would go about splitting equity fairly (11:24)

Apr 29, 202021:26
Setting A Yearly Company Vision & How To Get There

Setting A Yearly Company Vision & How To Get There

I was asked in my private slack community, Service Based Businesses:

- What do people use in terms of a system or prompt or format to remind themselves about their vision for their company, and the exciting goal they are working on?

- How can you plan your weekly, monthly, quarterly, yearly goals more visually?

Join the group & get access to answers like this and resources like the ones described in the podcast.

Apr 29, 202022:34
How To Generate New Business Through Channel Partners

How To Generate New Business Through Channel Partners

People ask me all the time: How do you get new business?

And I wish I could tell you there’s some magic trick or a super awesome FB Ads formula…

But it’s actually really simple: referrals and partnerships.

In today’s podcast,

I dive into the strategic approach for channel partnerships we used at Jakt to funnel new business,

and the steps you should take to build your social capital.

I’ll touch on:

- How I got new business when I started Jakt with no money (2:14)

- Why time and cost constraints lead to creativity in finding new customers (3:35)

- How we applied channel partnerships as a software agency to funnel new business (4:55)

- How referrals allow you to draft trust from the beginning and increase close rates (8:18)

- The different types of people that you can partner up with (9:09)

- The downsides to referrals (12:11)

- One of the best ways to form a partnership with someone (15:05)

Apr 29, 202019:54
Dealing with Loneliness as a CEO

Dealing with Loneliness as a CEO

Some people don’t understand how lonely and difficult it can be when you’re the head of the company.

If you’re a business owner, you might know what I’m talking about.

No matter if they are friends, family, or employees...

...a lot of them might struggle to grasp the difficult challenges you’re facing:

How you’re feeling, the risks you are going through, the stress...

In this episode, I dive deep into discussing how lonely it can get when you’re the CEO.

I’ll touch on…

- Why don’t most people understand how it feels to run a business (2:05)

- The need for empathy between you and others for not understanding it. (2:40)

- How inherent risks leverage the rewards for CEOs disproportionately to employees. (3:17)

Apr 29, 202010:33
How Much Should You Pay Yourself as a Business Owner

How Much Should You Pay Yourself as a Business Owner

As a business owner, it can be hard to decide how much you should be paying yourself.

All the profits? Just a set amount every month?...

In this episode,

I’ll share with you what I’ve been doing for the last 7+ years. I truly believe that this is something that has helped me grow Jakt from 0 to a $4M/year agency.

Here’s what I’ll touch on:

- Why taking only the bare minimum is the best decision to make from a financial standpoint (3:01)

- The best possible investment you can make when you’re starting (3:22)

- The big “mistake” people make when taking profits out (6:34)

- [Funny story] The longest I’ve gone without taking money (11:21)

Apr 29, 202025:14
How (And Why) to Get Started in Real Estate as a Business Owner

How (And Why) to Get Started in Real Estate as a Business Owner

Over the last 7 years, I started Jakt from scratch and grew it to a $4M/year business.

Now, I’m also following one of my passions for a long time: real estate.

In this episode,

I talk about real estate and passive income, the steps I’m taking to educate myself, and why I think business owners can find value in it.

I’ll touch on:

- My definition of passive income and how Real Estate relates to it (3:26) - Part 1

- Where I’m personally looking to invest in the near future (9:51) - Part 1

- How I’m studying and learning about it (5:18) - Part 2

- Why is wealth concentrated at the top circles, and how you can gain access to them (7:14)

Apr 28, 202026:12
How to Attract Customers Organically + Authentically

How to Attract Customers Organically + Authentically

Something that I get asked quite often is how we’ve grown Jakt from 0 to a $4M/year business.

If they’re expecting me to uncover a quick and easy strategy, they leave disappointed.

In this episode, I am sharing with you the exact way I use to bring in leads and new business to my companies.

The truth is, it takes work. And effort. And patience. But it has worked really well for me.

If you want to learn how you can apply this and how that can make a big difference to your business, make sure to listen to this podcast.

Here’s what I’ll cover:

- The interesting conversation I had where we uncovered why people don’t like this strategy 0:42

- The exact process I use to develop New Business (all steps) 3:55

- The value of compounding and the need for patience 5:25

- Why you should constantly be telling your story to the world 6:00

Get the book Give and Take: Why Helping Others Drives Success by Adam Grant here:

Apr 28, 202013:14
When (And How) to Fire an Employee

When (And How) to Fire an Employee

In this episode, I want to answer a question I received on how I decide to fire someone and how to do it. 

It’s an extremely complicated thing that doesn’t necessarily get easier.

Funny thing: it took me 6 months to build up the courage to fire someone for the first time. 

But there are certain things that I’ve picked up along the way that can help you make this type of decisions. 

In this segment, I’m sharing with you the real-life tactics and I hope you can take advantage of them and use them in your business. 

Here’s what I’ll touch on:

A story on the first time I fired someone 1:20

The one question you need to ask yourself before you pull the trigger 5:30

Culture vs. Performance-related reasons 6:20

How to legally protect yourself as a small business owner 11:15

Is there a “best” day to do it? 18:20

The emotional component to firing people 21:20

Apr 28, 202027:13
Changing Jakt’s Direction and Pivoting as A Company

Changing Jakt’s Direction and Pivoting as A Company

We are moving things and reinventing ourselves at Jakt!

In order to continue evolving, we believe that it’s important that we narrow our focus as a business. Really exciting times are coming.

In this episode, I talk about how to pivot your company and steer a moving ship, what it means to the current executive team, and how important your people and culture are during times of transition.

- The one challenge we are facing at Jakt that’s making us go even more narrow 3:00

- Applying the lessons I preach to other business owners 5:20

- Why E-commerce customers are extremely attractive for us 10:00

- Auditing our team before future changes 13:02

Apr 28, 202017:27
Walk The Talk: Radical Honesty and Practicing What You Preach

Walk The Talk: Radical Honesty and Practicing What You Preach

In this episode:

This episode is NOT for do-as-I-say, not-as-I-do fakers. I am sharing exactly how I am applying in my own businesses everything I put out on my content. In a completely transparent way, I will show you all that happens behind the scenes while taking a step forward against this trend that has appearance over reality.

- How I share what I’ve learned over the years 1:37

- How I share what I wish what I would’ve known when I was starting out 2:42

- Retracing my steps in getting a business off the ground 5:52

- Offering your product to the market 7:03

- Why you only need to focus on what you’re offering 11:25

- When you should say “no” 13:02

- The ambiguity in pricing 15:30

Apr 27, 202019:30
Sales Does Not End When You Close The Deal

Sales Does Not End When You Close The Deal

In this episode: 

What happens after you sign a new client? How do you manage all the little details throughout the entire relationship? In this episode of Reflections of a CEO, I’m walking you step-by-step on how our sales process works, what you’re really selling, how to sell through your service, and much more!

- Summing up sales 1:07 

- Selling through your service 2:23

- Defining “onboarding” 3:49

- Acknowledging a transition 7:33

- Sell them on the company, not on you 8:47

Apr 26, 202014:54
Why Do Employees (Really) Stay At Your Company?

Why Do Employees (Really) Stay At Your Company?

In this episode: 

What makes people stay at your company? Is it the mission? Your vision, maybe? What made them join in the first place? In this episode, I talk about what makes a company appealing to current and future employees, the importance of fostering a positive culture, and what keeps me at my company! Check it out!

- Diagnosing the divide between management and everyone else 1:23

- Why is it that people stay at a company? 4:36

- What makes me stay? 10:10

- What importance does the mission have in a company? 11:15

Apr 26, 202020:23
How Much Money Does An Agency Make

How Much Money Does An Agency Make

In this episode: 

For this episode of Reflections of a CEO, I’m joined by Jakt’s President, Cody Musser, to talk about our 2018 financial report. Join us for a look behind the scenes where we hold nothing back: including our exact revenue, expenses, and profit. 

- Why we share our financial reports with you 0:32

- Hitting the goal for 2018 2:40

- Accrual v. cash 4:05

- Breaking up your leftovers 19:06

- How much is allocated to marketing 21:58

Apr 25, 202037:02
How To Have Balance In Life & Business

How To Have Balance In Life & Business

In this episode:

Business is a long game. Here’s how CEOs and business owners can prepare --mentally, emotionally, and physically-- to play it for decades. It’s a marathon, not a sprint. In this episode, I discuss optimizing yourself, knowing your limit, and being very mindful your time.

- Context of my week 0:18

- Breaking up optimization into three parts 1:45

- Choosing who you surround yourself with 7:45

- Asking myself, “Am I productive or am I busy?” 9:31

- Pay attention to what your body needs 12:14

Apr 20, 202016:40
Here’s What I Do When “Everything Sucks”

Here’s What I Do When “Everything Sucks”

In this episode:

There will always be times that you won’t be on your game. In this intimate episode, I talk about getting back on your feet, avoiding burn out, and self-awareness. If you’re an entrepreneur or a CEO, you’ll get new ways to deal with adversity when running a business.

- What it’s like to experience this in business 0:58

- Becoming more self-aware 3:17

- Finding things that work for you 4:44

- Dealing with what’s bothering you 8:53

- Coping with loneliness in entrepreneurship 15:30

- Being in a good mindset for your own benefit and your business’ 18:01

Apr 20, 202020:43
Introducing Polpo Finance: A New Polpo Group Company

Introducing Polpo Finance: A New Polpo Group Company

In this episode:

I am tremendously excited to introduce the newest Polpo Group company to the world. I talk about how we will bring radical value to agencies, automation, the power of experience, finding markets, and much more!

- Some context for Polpo Group 1:10

- The new business under Polpo 1:54

- Finding a market for agencies 6:08

- Testing price models 12:48

- The benefit in Polpo Group 18:06

- Why I’m documenting this development 25:28

Apr 20, 202028:00
Jakt’s Initiatives for 2019

Jakt’s Initiatives for 2019

In this episode:

Cody Musser joins me for a special edition of Reflections of a CEO. In this episode, we discuss how we plan and strategize at Jakt, defining objectives, and holding ourselves accountable - even when it sucks.

- What makes a good initiative? 2:27

- How many initiatives should a company have? 9:55

- Jakt’s 3 initiatives for 2019 12:41

- Proactive vs. reactive outreach 15:49

- Improving the quality and capability of our work product 18:35

- Reducing monthly downside potential 23:25

- How to break up your initiatives into manageable chunks 31:15

- How to approach your initiatives so it’s not overwhelming 34:06

- Good actions you should take 48:30

Apr 20, 202053:03
What is The Polpo Group?
Apr 13, 202021:47
The Law of Attraction

The Law of Attraction

Taking steps forward in life often comes from 180 mindset shifts. In this episode, my girlfriend Sasha and I talk about the Law of Attraction, how you can rewire your thinking to achieve your goals, and the importance of executing.

Jan 12, 201933:21
Why Traditional New Year's Resolutions are Bullshit and How I Do It Instead

Why Traditional New Year's Resolutions are Bullshit and How I Do It Instead

New Year’s Resolutions are a common thing for people to do. Yet, so many people don’t stick with them. Why is this? In this podcast I explain my take on why this is the case and how I’m structuring them for 2019 in a unique way.

Jan 10, 201936:49
What It’s Really Like to Date an Entrepreneur

What It’s Really Like to Date an Entrepreneur

In this episode of Reflections of a CEO, my girlfriend Sasha joins me to help answer questions about what it's like to date an entrepreneur.

If you're an entrepreneur, date one, or are thinking of dating one, I think you'll enjoy this

Jan 04, 201901:03:32
2018 Accomplishments

2018 Accomplishments

Haven’t made a podcast in the past four months. 

But now I’m more than ready to start up again to kick off 2019. 

This podcast episode will get you up to speed on everything that's been going on in my life and with business over the past 4 months.

I also cover my biggest accomplishments of 2018 and what I'm excited about in 2019.

Jan 01, 201947:55
Anxiety & Entrepreneurship

Anxiety & Entrepreneurship

Anthony Tumbiolo talks about dealing with anxiety.
Jul 28, 201811:11
Working on the Business vs. Working in the Business

Working on the Business vs. Working in the Business

Anthony Tumbiolo talks about working on versus in the business.
Jul 25, 201815:30
Q2 Financials Recap

Q2 Financials Recap

Anthony Tumbiolo talks about Q2 financials.
Jul 23, 201810:28
Adjusting & Executing

Adjusting & Executing

Anthony Tumbiolo talks about adjusting & executing.
Jul 20, 201819:49
Acknowledging & Respecting Negative Emotions

Acknowledging & Respecting Negative Emotions

Anthony Tumbiolo talks about dealing with negative emotions.
Jul 18, 201808:50
Looking Towards the Future

Looking Towards the Future

Anthony Tumbiolo talks about building for the future.
Jul 16, 201813:28
Culture: Arguably Your Best Investment

Culture: Arguably Your Best Investment

Anthony Tumbiolo talks about culture.
Jul 13, 201822:48
Emotions Vs. Intellect

Emotions Vs. Intellect

Anthony Tumbiolo talks about emotions and their role within intellect.
Jul 10, 201812:55
Restructuring for Growth

Restructuring for Growth

Anthony Tumbiolo talks about restructuring for growth.
Jul 09, 201813:52
Burnout & Reflection

Burnout & Reflection

Anthony Tumbiolo talks about reflecting on being stressed out.
Jul 06, 201810:12
Scaling Jakt

Scaling Jakt

Anthony Tumbiolo talks about restructuring Jakt.
Jul 04, 201809:12
The Mission

The Mission

Anthony Tumbiolo talks about the mission of Jakt, as well as his own personal mission.
Jul 03, 201817:11
Investing Into My Business

Investing Into My Business

Anthony Tumbiolo talks about investing back into his company.
Jul 02, 201811:22
Jakt Hiring - New Division

Jakt Hiring - New Division

Anthony Tumbiolo talks about the new division at Jakt
Jun 25, 201809:39
We Closed the Gap!

We Closed the Gap!

Anthony Tumbiolo talks about how the team closed the gap for June.
Jun 24, 201811:10
Tokenization & Closing June's Sales Gap

Tokenization & Closing June's Sales Gap

Anthony Tumbiolo talks about tokenization and closing next month's sales gap.
Jun 23, 201807:00
Bringing the Team Together

Bringing the Team Together

Anthony Tumbiolo talks about bringing the team together.
Jun 22, 201810:07
Why Reinvestment is Key

Why Reinvestment is Key

Anthony Tumbiolo talks about reinvestment in a service based business.
Jun 21, 201812:15
The Long Term Game

The Long Term Game

Anthony Tumbiolo talks about the long term game of service based business.
Jun 20, 201807:49
Blockchain, VR & Voice

Blockchain, VR & Voice

Anthony Tumbiolo talks about blockchain, voice and VR.
Jun 19, 201832:10