A Meta-Perspective On Living Through The Lens Of Tech Entrepreneurship

Everything is in a startup: time management, relationship-building, finance, sales, marketing, programming, investment banking--the list goes on. It's more than a little like life because when you're building a company you really do have to take everything into account to be successful.
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Calm and understated, I almost walked past Peter Sinkevich at a summer Entrepreneurs' Roundtable Accelerator networking event this past summer. I'm glad I didn't. Aside from the fact that his successes in serial entrepreneurship and venture capital made him an early millionaire at the age of 20 via exit, or that his exploits are more characteristic of people 20 years his senior, Peter has the uncommon virtue of having developed a meta-view of living life through the lens of tech entrepreneurship. Some might call this extreme, but this blogger thinks it's remarkable.

I sat down with Peter a few weeks ago to get some added perspective on Peter's view of life and how he infuses startup principles into his daily living. The answers I received to my questions can help not only entrepreneurs, but anyone looking to operationally optimize their day-to-day. Our interview, below:

Why choose the startup as a template for better living?

Everything is in a startup: time management, relationship-building, finance, sales, marketing, programming, investment banking--the list goes on. It's more than a little like life because when you're building a company you really do have to take everything into account to be successful. So I thought, 'if the startup lifecycle is a microcosm of life, then life itself should reflect the way startups grow.' Both things require most of your energy, if you're at all goal-oriented; both things require you to learn from your failures to find success, both things require a combination of vision and execution to thrive. But while you only have one life, with startups, you can start again if you fail. Yet, even the learning curves and developmental time horizons for both are similar, because both things start, literally and figuratively, as an infant. Both need to be nurtured to grow. So you have a bit of catching up to do in terms of knowledge and such and so I think using the startup as a template for living can give people a sort of operational matrix for understanding when and how best to get over obstacles and optimize their day-to-day.

Can you give me an example of how this can work for the average person?

Sure. I get a lot of requests for help from Millennials seeking jobs at startups, or wanting to start startups themselves. I help them by asking them to test themselves for strengths every entrepreneur needs to succeed--for example, can you sell yourself effectively? Can you get a good understanding of who your audience is, and who you're trying to speak to and appeal to get that job? In startups and in job hunting, selling and marketing are necessary skills, whether in trying to market and successfully sell a product or market and successfully sell yourself for a job offer. Show the employer that you know about their problems, and demonstrate your ability to solve any one (or more) of those problems, and that's how to create value for any team and get hired, regardless of your level of expertise. If you can demonstrate that you can solve a company's problems, you are hirable anywhere.

What have been people's reactions to this idea?

Fairly positive. It's a very meta-idea, and also very niche to the entrepreneurial community, so the vast majority of people--even within the community--don't think to use these principles on everything.

Can you give us an idea of how it feeds into your current work?

Definitely! An extension of the idea into my current work is ILoveStartup.com, a new brand I've been nurturing under which I've been pursuing various projects intended to help entrepreneurs get the most out of their communities and execute better. One thing I think many entrepreneurs don't get, especially given we're living in a post-financial crisis world, is that startups and startup communities don't have to make their primary focus all about money. Companies doing social good help everybody.

How is what you're doing helping people?

A while back, I helped Startup Grind, the world's largest entrepreneurial community, powered by Google for Entrepreneurs, build their first chapter in Connecticut in Greenwich, CT. That led CT Governor Dan Malloy to call upon my business partner and I to create what is now ILoveStartup.com's venture fund, Stamford Venture Partners. Although a goal of the fund is to create alpha (returns above and beyond what is expected), its primary goal is to lead surrounding area investors and enrich Fairfield County, a part of the greater New York City region. Connecticut doesn't have a cohesive startup ecosystem like New York City, so we thought we would take a major role in creating one to both support CT-based entrepreneurs and attract high quality entrepreneurs to CT to do business. Also, CT's population has actually been on a continual decline for the past two decades, so we're hoping to attract entrepreneurs to Fairfield County, and then incubate and fund them. We believe that giving life to a thriving startup economy in Connecticut will attract people to do business here, then live here, then move here and raise their families here.

We're also focusing on sharing stories of entrepreneurial failure, arguably the most important conversation no one is having. This isn't to glorify screwing up, but rather to promote the reality that accepting failure is a de facto part of starting up (not to mention life), and that handling it in the right way, learning from it and using the learned lessons to pursue greater success makes you a better individual. My good friend Bob Dorf, the co-author of The Startup Owner's Manual, along with Steve Blank of Silicon Valley fame, introduced the concept to me. Dorf's Manual is one of the most important texts an entrepreneur can read, and after discussing this concept at length my team and I have Fuckup Nights, part of a global movement currently represented in 154 cities in over 50 countries and growing. It is receiving amazing attention, already covered in many major news outlets including the Huffington Post, and has enjoyed the participation of several high quality speakers like Y Combinator alum and Emmy Award winning founder Dan Albritton, Shark Tank featured founder Lori Cheek, and General Assembly co-founder Dan Hargreaves. We've been holding the events at Pivotal Labs every first Thursday of each month, but will expand our efforts beyond Chelsea to Brooklyn this fall, and, eventually, to CT.

To conclude, what core advice would you give to new entrepreneurs in this imminently more difficult business environment?

Rule #1: Remember that everything in life is a transaction. Every transaction has a point of sale. So living life is akin to selling to a buyer--the people you will interact with. But, you have to not only be valuable, but also likable to be able to sell yourself... after all, the number one rule of sales is that no one will buy anything from you if they don't like you first. The measurement of your success is what you can accomplish, which also depends on who you know that can help you achieve your goals, and only by being likable will people want to know you and help you in some capacity to achieve your goals, even if it's something as simple as a reaction, an email intro, or a contact point.

Rule #2: Don't sell to a market/demographic you don't understand. Your message and vernacular can be wildly off base from what the audience cares about--like landing a plane blindfolded... Scary. Don't develop ideas in a vacuum. Understand the audience attached to the problem your addressing first. They will clarify the details of the problem and what matters the most to them--the buyer, implicitly or expressly. In a job, while "treading water", meet expectations, and simultaneously take a lay of land regarding the people and the dynamic at hand, and understand what and who you're dealing with, and then make a plan of action of how to excel while navigating everything you discovered. Observe actions and see what everyone else is focusing on to ascertain goals, and then help them fulfill their goals that fall within your capabilities.

Rule #3. Execute well. Actions are more important than words. This goes back to a mantra I use to determine people's real intentions: "Your actions speak so loudly I cannot hear what you are saying."

Rule #4. Have a clear understanding of weaknesses and strengths--through a SWOT analysis or otherwise--and once you know those, surround yourself with people who are better at your identified weaknesses than you are and get them onboard at some level to increase your level of execution.

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