Learn, Digest & Get After It – Top 10 Books & Podcasts For Entrepreneurs

When I was practicing as an attorney prior to starting my own legal tech company, I never really thought of myself as entrepreneurial. At least, that was never how I referred to myself. Self-starter, convention challenger, generally informed and certainly opinionated – yes, those things always felt like me.

When both my attorney parents left their big firm and corporate jobs to start their own firms, I didn’t think of them as entrepreneurial either. For whatever reason, being “entrepreneurial” just wasn’t something I associated with being a attorney. It wasn’t until I left my corporate gig at Google that I realized that I come from a long, proud line of people that are both attorneys and entrepreneurs. It’s in my blood and I didn’t even get it. I know, duh.

The fact is, I’m not alone. More and more attorneys are challenging the traditional seven (or more) year partnership track and jumping ship to do what they want with their careers. If you play your cards right, having a law degree can be a stepping stone to wherever you want to go, whether it’s starting your own company (law firm or otherwise) or using your degree in some other, less traditional way.

After leaving Google, I did some soul searching and read and listened to a lot of resources about becoming an entrepreneur and starting a company. As the founder of Headnote, the journey to becoming the CEO of a venture-backed company has been anything but linear. But above all else, I use my legal skills and analytical thinking every. single. day. Fret not attorney parents, my law school degree was not wasted after all.

If you’re thinking of taking the leap, read on. It can be scary and weird and not at all paved with the certainty that the partnership track offers. But it offers so much more. You should go for it, but before you do, read and listen to my selections below that can offer a crash course in starting your own adventure…

1. Eric Ries: The Lean StartUp

Ah, the good old days. When I left Google to become an entrepreneur, this was the first book I was given by my startup veteran husband. I tore through it and still think of it often. If you’re thinking of starting your own company or want to understand the basics of running a lean business, this classic is the place to start. My biggest take away: your hypotheses are generally going to be wrong, so you need to learn how to test your assumptions with minimal investment and waste. Amazing lessons no matter where you work or what you do.

2. Tony Hsieh: Delivering Happiness

Another required reading as far as I’m concerned. Okay, so you’ve made the decision to start your own thing and have gotten down the basic vocabulary and lessons. Now it’s time to get inspired to kick some serious ass. Tony Hsieh’s story of how and why he started Zappos is just that and it really illustrates how to apply lean ideas to a real business. Guaranteed to make you feel proud and positive about your decision to make the leap.  

3. StartUp Podcast Season 1: Gimlet Media

Alright, you’re feeling p-r-e-t-t-y good about your decision. Now it’s time to give you a small dose of real life via this fantastically entertaining non-fiction podcast about the trials and tribulations of starting your own company. You’ll laugh, you’ll cringe, you’ll wonder if this is the right decision for you after all. This is a great test because if you’re really meant to survive as an entrepreneur, you’ve got to be resilient. Remember, if it was easy everyone would do it.

4. Simon Sinek’s Ted Talk: How Great Leaders Inspire Action

Okay, you get it. This isn’t going to be simple and it’s probably going to get much harder before it gets easier. Now let’s pick the energy back up and remind ourselves that we can do this. If you want others to follow you, you’ve got to inspire them. Great leaders ask why, so you’ve got to learn how to realign your thinking and stick to the Golden Circle. “What is your purpose, your cause, your belief? Why do you get out of bed in the morning? And why should anybody care?” If you can answer these questions, you’re in the right place and on the right track.

5. Porter Gale: Your Network Is Your Networth

Alright, we’ve heard some horror stories, learned some basics, got inspired and remember why we’re on this path in the first place. Now it’s time to find your tribe. Who can you rely on to help you along the way? Who do you already know that can offer you advice? What can you learn from your network? You can probably extract more value than you think. But first, we need to figure out how to tap into that value. Tapping into your network for resources and wisdom is critical as an entrepreneur, and really, your network is everything.

6. Brad Feld: Venture Deals

This book has essentially been my startup bible for the last few years, through experimenting with businesses that just weren’t right for me, to finding my perfect fit at Headnote, to negotiating (and understanding) my first term sheet from a VC firm in Silicon Valley. I basically carried this little purple book with me everywhere I went for a solid year. If you’re thinking of going the venture route, please read this book. Not only will you learn a ton, you’ll probably save yourself some embarrassment at a pitch meeting somewhere down the line.

7. Amy Cuddy’s Ted Talk: Your Body Language Shapes Who You Are

Now that you’re inspired and thinking like a strong, smart, entrepreneurial leader, it’s time to act like one, too. Most people don’t realize that raising money is essentially like being an actor – you’ve got to become really secure with yourself and your vision and get rejected much more often than you’ll hear people say yes. You’re not going to be able to convince investors they should believe in you if your body language isn’t totally on point. This talk is amazing because it reminds you that the little things you do with your physical body can have a huge effect on your mental state. By training yourself and harnessing your physicality you can be way more effectual than you thought.

8. Jack Welsch: Winning

For all the 30 Rock fans out there, the time has come to harness your inner Jack Donaghy. Jack Welsch was the Chairman and CEO of General Electric for 20 years and he’s pretty much seen it all. What I love about his book about corporate leadership is it really spells out exactly what to do when hiring, evaluating, letting people go, etc. It’s really instructional and perfect for highlighting and underlining – now there’s my inner nerdy attorney coming out!

9. Dan Ariely: Predictably Irrational

Just when you think you’ve got it all figured out, people do exactly what they shouldn’t. Dan Ariely’s book offers great insight into why people do what they do and how you can spot the patterns in even the most seemingly irrational human behavior. These lessons are extremely relevant when making a product or company and trying to figure out how people are going to react. Pro tip: it’s probably not going to go how you thought it was. Read this to be ready and prepped for the unexpected.

10. Ben Horowitz: The Hard Thing About Hard Things

Okay, you’re almost there. You’ve made the jump, came up with your idea, learned the basics, inspired anew, built a team, and found investors. You’ve got a real company. But the hard part is just beginning, and Ben Horowitz’s book offers great lessons in remembering a simple point: the hardest part is when things are hard. You’ve got to persevere, be resilient, and learn from others as quickly as humanly possible. If I’m ever questioning myself or my decisions during the hard moments, this is the first place I turn. If Ben Horowitz and Marc Andreessen worried when things got tough, then I’m in good company. If nothing else this book can inspire you to keep going when you hit a rough patch.

I hope you’ve enjoyed my compiled list.  Happy summer reading!

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