"I was so confident that I would have no problem within the 3 months of me moving back, of just starting a business and making bajillions of dollars from it. I didn’t really truly understand what it meant to start a business."

Anthony Sistilli is a web developer and former top 200 Starcraft player. He originally worked as a software engineer at Intuit and quit his job after 9 months to pursue his… Many pursuits.

These include a dropshipping store which he grew via Instagram and without any advertising. He founded The Forge, a community to help students get software engineering jobs and prepare for interviews which he grew to 7,000 members within 2 months with zero advertising. He was one of the youngest consultants on Toptal, a competitive premium freelance platform.

These days he’s continuing his software consulting to fund micro-ventures and business experiments including trying out affiliate marketing.

In this episode we talk about how he got his job at Intuit just 8 months after learning to code and almost dropping out of his engineering program. We discuss how becoming one of the best Starcraft players taught him about entrepreneurship. We also dive into what it felt like to be in debt when he first quit his job, living in AirBnBs all over Toronto before he decided move back in with his mom.

We also go into his operating and decision-making system in this wide-ranging interview. We cover how he decided whether or not to quit his job cold turkey to pursue business, his morning routine, and how he views unpleasant circumstances and resets his perspective.


Listen to the episode on Apple Podcasts, Spotify, or on your favorite podcast platform.

Listen on Apple Podcasts  | Listen on Google Play | Listen on Spotify

Roxine’s Notes from the Interview

  • Anthony has an obsessive, focused nature
  • He felt relief after allowing himself to switch goals
  • It’s OK to switch goals!
  • Don’t quit until you have something going on (for most people)
  • Wait until your side hustle makes as much as your main thing
  • Anthony saw risk differently, but could also stomach a lot of risk
  • Entrepreneurs perceive risk differently, but may not necessarily be bigger risk-takers
  • For Anthony, not growing is riskier than quitting a job with a regular income
  • He would rather spend a summer doing and learning on his own, than spend it in a job that paid, but was mediocre. The risk isn’t a monetary risk. The risk is a competence risk.
  • Entrepreneurs aim to get 2x or 3x the reward for the risk they’re taking on
  • Double- or triple-dipping to hedge bets
  • Research paper to back that up When it comes to evaluating risk, [knowing] what you want to get out of it is a huge factor.
  • The good to great mindset
  • He was willing to let go of good so he could reach for great: Intuit. A lot of people were getting internships. And a lot of the time people would get internships that were not the best, but they were something. And a lot of people would rather have something than nothing.
  • Self-reflection and self-awareness
  • He journaled every single night for 6 years before he went to bed
  • He uses The 5-Minute Journal and meditates
  • The value of solitude That self-reflection has helped me get to where I am and help me realize the importance of growing as a person and growing your mindset.
  • Learning to work with your conscious and subconscious mind, whether as a technical professional or a creative
  • Doing VS Being entrepreneurship
  • Do you want the title or do you want to be one?
  • Anthony admitted to himself that he had to move back in with his mom for a year because his businesses weren’t going so well “I was so confident that I would have no problem within the 3 months of me moving back, of just starting a business and making bajillions of dollars from it. I didn’t really truly understand what it meant to start a business.”
  • When you’re bootstrapping or starting out, you probably have to take on jobs that aren’t creatively-fulfilling to make ends meet until you can live on creatively-fulfilling work. Hav humility and a good attitude towards that.
  • Be humble enough to do that
  • Question your belief systems
  • Does this belief help me?
  • How does this hurt me?
  • Why do I have this belief?
  • Can pay and will pay
  • Students aren’t a good demographic to target
  • Went “back” to consulting
  • To get capital for businesses
  • He doesn’t have to rely on one business to fund his other ventures
  • Started consulting with Toptal
  • Good way to get started with consulting
  • Imposter syndrome
    ”My confidence isn’t as much in my software engineering ability as it is in my ability to adapt and learn on the fly as I go. Even if I take a job that I have zero understanding on what’s going on I’m very confident that I’ll be able to bring myself to that level without compromising the quality of the work I’m doing.”
  • How he stays organized without being routine
  • At least 8 hours of sleep
  • How he gets himself up to a good state through his morning routine
  • A quick workout
  • Write in his 5-Minute Journal
  • Meditate
  • Focusing on the negative feeling and distances himself from it
  • Focusing on what you want out of life and feeling of abundance
  • Accepting negative feeling: You choose how you it affects you
  • It doesn’t have to influence how your day goes
  • “Today would be awesome if…”
  • Look for the fun, and less on the productivity
  • He doesn’t give himself due dates
  • Structured, yet unstructured. Routine, yet no routine philosophy ”A lot of my day is making sure that the things I have fun doing are in line with what my goals are… Figuring out how I can make it so I want to do [it] and make it fun and exciting for me.
  • Scarcity vs Abundance
  • Believe in what you can do, regardless of where you are now or the cards you were dealt
  • Get rid of the “Yeah, buts…”

”When you have that type of belief, it’s a scarcity belief. You believe that it’s very hard to do something or your skillset is very limited to achieve something, that you’re in scarcity of this thing. And when you go through life with this lens in front of you, you’re going to be crossing off possibilities that you didn’t know exist before you know they exist.”

”I think 2 hours in a really good mental state, is better than 10 hours in a really bad mental state.”

Productivity, to me, is not about how many hours I put in. It’s about the mind-state I’m in when I’m putting those hours in.

Selected Links from the Episode


People Mentioned


What Next?

If you enjoy the stuff I dig into in this podcast, then I can pretty much guarantee that you will enjoy my blog.

Drop in your email below, and you’ll get access to subscribers-only content, offers, meet-up’s, and AMAs with guests.

No fluff, no spam, no negativity.

Peace out, fam.