Hi, I'm Dale - let's work together :)

I love helping first-time entrepreneurs identify their core values, learn to love themselves (flaws included!) and make the difficult decisions necessary to build a wildly successful businesses.
I know the journey because because I've lived it myself: I was one of the first Thiel Fellows and ran UnCollege for six years before selling it in 2016. Along the way, I wrote a book Penguin published, started investing, and trained with one of the most experienced coaches for technology entrepreneurs.

My clients are entrepreneurs, founders, and leaders working in early-stage companies. Entrepreneurs bring a unique perspective to the world, and are some of the most interesting folks I've ever met.

As a coach, I offer my clients guidance, skill building, mentoring, and perspective grounded in years of seeing successful companies built from the inside. Our work together will identify your most challenging issues and transform them into strengths across your business and your life.

Every client engagement is different, but these are the areas I usually focus on:


Whether we are building a vision of your career and your life from scratch, or clarifying a path you're already on, we will paint a detailed picture of where we are headed together. Who am I? What are my values? Which of my beliefs might be holding me back? Simply knowing exactly what you are headed is a powerful catalyst, and drives our work in the next two areas.


The business issues—such as organization, strategy, measurement targets, processes and road maps—are the easy stuff of coaching. This is the part where I act as your personal COO. What is the path, how do you choose between options, and what steps do you take next? What will you commit to in the next week? What might get in your way, and how can we plan for that? How can I hold you accountable? These are the nuts and bolts where we figure out what’s most important to accomplish now and ultimately drive productive and decision-making.


A lot of people think that being successful is about working as hard as you possibly can. While it’s clear you need to do good work, it is imperative to understand your own beliefs, resistance, and patterns. Working together, we’ll uncover how you think, what leads you to act (or drag your feet), and how to optimize for the things you want. This is something that is particularly hard to do alone – the thought partnership a skilled coach provides can get you through resistance and confusion much faster than you can do it yourself.


It's time to launch a product, build a community around your brand, get national media attention to attract investors, or put your CEO in front of the right stakeholders?

I designed and executed campaigns that got my work featured on every major media outlet you can think of - Today Show, Morning Edition, Katie Couric - and built an internationally recognized brand in education, without spending a dollar on PR.


Need a [keynote speech, investor deck, press release, thought leadership article, blog post, sales collateral, ad creative,  overall content strategy, or any other written material]? 

I've given more than 200 public talks, raised $2M for my own projects, and written for the NYT, WSJ, and Washington Post (among many others). Also, Penguin published my book, Hacking Your Education, in 2013.


You just raised money and need to figure out the game plan? You need to figure out how to increase revenue without increasing your sales/marketing spend? You need to decide between whether to raise money, or bootstrap, and what the story is if you do?

Companies I advise have raised more than $45M, I've been the catalyst for key hires that led to successful acquisitions, and made introductions that resulted in two exits.

Does it sound like I can help? Email me and let's chat!

Advising & Consulting Clients

I've worked with large companies (Intel, Agilent, NBC Universal, Malaysian Ministry of Innovation), startups (Degreed, NextBillion.org, WellTrack, Roikoi, Jobstart, Loomia, Sunrise) and agencies (Ready State, Institute for the Future). You can find a formal list of my work on my LinkedIn profile.


I like startups that are real businesses. They have six figures in revenue (and growing), sell a product/service for a profit, and have a clear path to being able to triple invested capital.

I love working with early-stage founders. I write small checks personally, but have access to larger amounts of capital through a family office. I'm always open to hearing about investment opportunities -- the best way to contact me is to drop me an email: dalejstephens@gmail.com

A few examples: Loomia, Beelightful, Cleveland Whiskey (see them all on Angel List)


I've given more than 200 public talks around the world - from TEDxTaiwan to the New York Times. If you're interested in hiring me to speak, email me and I can put you in touch with my agent.