Trep Life Interview with Justin Milano

Malachi Leopold, Co-founder of Trep Life, interviews Good Startups co-founder Justin Milano to gain some deeper insights into what inspires Justin and the culture he helps to foster in the startups he coaches.  

Q: What was the inspiration for Good Startups, and what is it all about?

Funny enough, I did not intend to create Good Startups. What happened was entrepreneurs began reaching out for business and leadership coaching. As I began supporting entrepreneurs, I realized how much I loved what I was doing. I began recognizing that entrepreneurs needed as much support with navigating the ups and downs of entrepreneurship as their business model. Thus, we have brought together a team of exceptional coaches to help entrepreneurs grow their self awareness, expand their leadership skills, and build thriving companies.  

Q: You’ve been a founder, hired CEO, and coach - what do you love the most?

For me it’s being a founder and coach. As a founder you have the opportunity to create something from the soil of your soul. Something uniquely you. As a coach I have the opportunity to be of service. I am not going to be a billionaire being a coach, but when an entrepreneur makes a big leap in their consciousness and business because of the work we are doing together, I get a feeling that cannot be described in words. I guess that is why Good Startups is perfect for me, because I get to be a founder and coach.  

Q: You’ve been through Gay Hendrick’s coaching program - what did you learn?

Gay and Kathlyn Hendricks are two of the most authentic people I have met. Who they are and what they teach are in perfect alignment. That is inspiring to me. What you learn in the Hendricks Leadership program is a masterful practice of integrity. This sounds simple on the surface, but it is truly a life-long practice to embody integrity as a person and leader. Their four pillars of integrity are authenticity, emotional intelligence, healthy responsibility, and agreements. When you master those four pillars, your life flows in all areas.  

Q: You’re an advocate of the idea that entrepreneurs don’t have to “kill themselves” to get their businesses off the ground. The belief that 18 hours days for months on end are unavoidable in the startup phase - this is a belief you don’t subscribe to. On the opposite end of the spectrum, Elon Musk says work 120 hours a week and accomplish in 4 months what it takes others a year to do. Discuss.

Elon Musk is one of the most brilliant people of our time, so I am appreciating having the opportunity to answer a question like this. What I have found is that when you are operating from your core values and fulfilling your unique life purpose, you have a reservoir of energy available to you that allows you to stretch beyond what is seemingly possible. That said, I am also a strong advocate of listening to your body. Sometimes you have energy, and sometimes you need to rest. When you align with the rhythms of your body and cultivate the ability to focus on what’s actually important, 18 hour days become optional. For me, the success of my life will not purely be measured by my career in the public eye, but also the success of my relationships, family, and the ability to experience all this world has to offer. And most importantly, the success of my life will be measured by the growth of my consciousness.

Q: You’ve said that the existing VC model is broken - with data showing that the majority of returns are being realized by a small percentage of VC’s. But isn’t that just the 80/20 or 90/10 rule at work? Meaning, isn’t that every sector, every situation? For example, in sales, 80-90% of the revenue is generated by 10-20% of the sales team. In the VC world, should we expect any different? Or, is the model actually broken?

Yes I appreciate the 80/20 rule, and I also believe it is possible for entrepreneurship as a whole to evolve beyond the results of the past 20 years. What would our world look like if 50% of entrepreneurs failed instead of 90%? There are accelerators like YCombinator that are offering some of the best business coaching in the world to early-stage entrepreneurs, but they are still reporting high failure rates. There is something else driving the high failure rates and excess waste of venture capital, and my sense is that “pressure capital,” or the need to grow quick and sell early, plus entrepreneurs building companies that are not fully aligned with their true motivation are recipes for a broken system. These are the types of big questions that are motivating the team at Good Startups.     

Q: You’ve engaged an awesome team for Good Startups - give us a quick rundown of the roster.

We have my co-founder Dan Cordaro from the Yale Center for Emotional Intelligence, which is arguably the number one emotional intelligence research center in the world. What’s unique about Dan is that he is a master of human emotion, and he is an entrepreneur working on his own projects like Good Startups and his non-profit Contentment.org. Dan has read every major spiritual text of our time and is a translator of ancient wisdom into the modern language of our time, science. What’s also great about Dan is he is helping us measure the impact of our coaching so we can provide empirical evidence that will inspire entrepreneurs worldwide to seek this type of support.  

Abby Stason is a Senior Coach at Facebook where she teaches Mindful Leadership practices to Facebook’s key team members and executives. Abby has 40,000 hours experience leading teams.

Finally, we have other leadership coaches who offer organizational design and business coaching to support entrepreneurs in building thriving companies. We truly have a roster of exceptional coaches and human beings. I feel honored that I get to collaborate with such wonderful people each day.   

Q: Facebook and other high growth companies utilize executive coaching for their entire team - how can smaller companies leverage the value of coaching while working on a bootstrap budget?

We have found a way to make $1,000 per hour leadership and business coaching available to early-stage entrepreneurs by using technology and small group coaching through our Breakthrough Program. We feel that every entrepreneur faces “breakdown to breakthrough” moments on the journey, and that by having us here to support you in critical moments your chances of success increase exponentially. You just need to get over the stigma of being supported. Every great entrepreneur has a support system, even if they are not public about it.  

Q: What’s a tip for someone who’s at a crossroads, such as facing the need to pivot, rebrand, take an opportunity? These times are often full of tension and worry, and the feeling of a complete lack of headspace. What can someone do to give themselves the ability to focus and intuit, and explore the path that will feel most authentic to them and their company?

First, what if you approached the situation as if it had already occurred and no matter what happened, you would be ok? The first step is to presence the intense fear and anxiety that is underneath the big choices. When you lean into and breathe with your fear there is great wisdom to discover underneath the energy of fear that normally leads to your answer.  

Furthermore, I find in these major choice points entrepreneurs normally get stuck in their head, doing an analysis of all the pros and cons. While analysis is valuable, even more valuable is your gut intuition. Your body and soul already know the best path, and your job is to simply open to the answer. Suffering only exists when we resist “what is.” We can spend months trying to avoid the truth of our experience, but it will find it’s way to the surface.

So finally, remember there is no such thing as a wrong choice. There are only choices. I have found to let go of regret for past decisions and instead see them as perfect on the path of my unfolding as a human being. Life is a big game, live it with curiosity and open to what wants to happen next. Trust.    

Q: As I did, you changed your name - actually, you went a step further and changed both your first and last name (I only changed my middle and last name). In Kabala, there’s a saying: change your name, change your destiny. How’s it been in the first year of living with a new name?

Great question! My name change came through during a meditation weekend in Santa Barbara. I cannot imagine being in a better place than I am right now in my life. This is not to say I am not experiencing challenges (I have many), but right now I feel more aligned in who I am than ever before. I appreciate you giving me the opportunity to reflect on that.