Entrepreneurs are perpetually interested in M&A and Venture Capital topics, but often have little direct experience themselves. The math behind this is pretty obvious: if an entrepreneur starts 3 or 4 startups in his career, there are only so many opportunities that an entrepreneur gets to learn about these kinds of deals.

On the other hand, the people who work inside of Corporate Development (those who do M&A deals as their job) and Venture Capital see hundreds of opportunities a year. To an entrepreneur, it is a big deal. On the other side of the table, it is just another day on the job. 

This week on the podcast we talk to Tim Porter (@tmporter), managing partner at Madrona Venture Group and former investor in my startup, AppFog. Before that, he worked at Microsoft doing M&A and Corp Dev which gives him a lot of perspective that many entrepreneurs don't have. We pick his brain and try to learn as much as possible this week.

Eliot Peper is pioneering the idea of startup fiction and has just released his second novel in the Uncommon Stock series. This week we get an exclusive behind-the-scenes view into the life of this author and his inspirations and motivations.

• Uncommon Stock: Book 1
• Uncommon Stock: Book 2 NEW JUST RELEASED!!

Espree is very honest about her fears of asking for money in this show and we discuss ways to manage and conquer that fear.

In the pre-show, Lucas and Eliot discuss Tony Robbins and wonder if he has any fears before his big talks. Tony Robbins just interviewed some of the worlds top money managers all around the world. He spent hours recording interviews, taking notes and learning from them. He asked their secrets and asked what the common person can do, when it seems the whole deck is stacked against you. He talks about what he learned in Tim Ferriss Show with Tony Robbins (View on iTunes) about his new book, Money: Master the Game. Lucas and Eliot discuss investment portfolios and talk about the book. Don’t miss this episode to hear all of the money conversation.

We then discuss the importance of investing in yourself. It can be through education (reading, courses, mentorship) or even by writing books. Monetizing books doesn’t have to be directly be selling them, the simple fact that you wrote a book could change your career. Most people underinvest in themselves after college is over. Having a bachelor degree is not a competitive advantage anymore.

Investing in yourself allows you to have some control into whether it achieves success or not. If you own Google, you can’t control how well it does. But if you start a business making sculptures and sells them on Etsy, and invest the money you would have spent on Google stocks into your own business, you would have some level of actionable input into the success of that venture.

Eliot’s first book, Uncommon Stock, came out last March, it is a thriller novel about a startup company. He doesn’t have huge checks coming in but has met some amazing non monetary benefits. He has met tons of leading startup CEO’s because they read it and enjoyed it. By investing in himself, it opened so many doors that would not have opened without it.

One thing unique to our generation is that the tools needed are a lot cheaper than ever before. There is a TED talk, J.J. Abrams: The mystery box where he talks about how you can make a movie like Star Wars, with a computer that a highschool student may throw away today. The tools are so much more accessible now.

2 Resources To Invest In Yourself (18:41)

James Altucher’s book, Choose Yourself! Tucker Max, Book In A Box(mention Lucas and receive a discount!)

Storytelling (19:38)

Eliot feels that people are still trying to figure out how to leverage audio and tell powerful stories with it. He asks Espree what some of the lessons are she has learned about storytelling.

She takes podcasting very seriously but always remembers to try and be herself. She tells us that so many people try to be someone else. She tells us that she heard that Tim Ferriss had terrible episodes for the first two, and maybe because he tried so hard to be the perfect podcaster. In the past, Espree has struggled to be the perfect entrepreneur. She tells me that she listens to her own podcast over and over again to learn from it.

She knows that she should not expect to be at the level of the podcasters she loves that have 15 years experience, overnight. Espree would like for you to take away from this show, to trust yourself and be yourself. She likes to really put herself out there and really struggles with the notion of making money from your art. There is this whole debate out there about if you can really make money off your podcast. She just opened a Patreon page, and it is not live yet, and she watched a really great TED talk by Amanda Palmer, the question is not about how to make people make money of music but how to let them pay for music.

Espree has been a bridge to help entrepreneurs with start ups and now she is starting her own podcast. She has fears about how to create a podcast and she has given herself a runway with has savings so she can really give this her all. She has never reached out to sponsors in her life, and has a lot of great questions about how to do so. She is so honest, and so passionate that you are going to want to watch the show to catch the whole story.

Lusas shares with us that there are two podcasts that he is a huge fan of that talk about this. One is Joanna Penn and the Creative Penn and another is Entrepreneur On Fire, with John Lee Dumas. He has a free resource guide for podcasters to help them with all these questions.

Eliot tells us that we don’t want to ask for money and people don’t like to be asked for money. People do like to be included, so if you can make them feel included somehow, that is a good place to start.

How Do We Get Past The Fear? (32:35)

Eliot gave her an off the cuff idea that she could perhaps sell tickets for people to view her recording the podcast. She asks, and the core of it is, how do you get past the fear? You need a ticket page,to set a price and then send it to someone you know. That is really hard to do.

Espree tells us that Lucas raised a ridiculous amount of money and asked Lucas if he had any mental blocks about whether he was worthy of that money. He tells us that everyday, he woke up scared and had an internal track in his head that told him it was a stupid idea and he needed to stop trying.

He was three months away from his son being born, when he quit his job. His wife didn’t work and he had no income or health insurance when his son was born. He didn’t get the money as quickly as he hoped, and it was three months after his son was born before he could start paying himself any salary at all.

It was the most scary time of his life. That moment was the most rewarding as well because that is when he realized that you can hear those things in your head and then decide. He tells us it is like standing on a rock and thinking about jumping in; you can think of two million reasons why you shouldn’t jump in. At some point, you give up on that soundtrack and do it anyhow. At some point you have to trust yourself and just go for it. You realize that the soundtrack playing is not a call to action but a recording on repeat; you close your eyes and jump in!

You will never convince yourself that it is a good idea to ask for money is because it is probably never going to be a good idea.

A lot of product entrepreneurs love AB testing their products. They have never thought about AB testing your life?

Espree learned early on that people can think that your product is not very good if it is free. She thinks that she will launch her page and talk about it with her audience. Maybe she will split test them, maybe it will work and maybe it won’t.

She asks, what is the worst that happens? She shares a story about a kickstarter cooler that never made it the first time. It was put on again, the cooler never changed but the way it was presented changed and they got something like a million dollars.

Podcasting has come up many times, but this information applies to all entrepreneurs. There may be a handful of people that don’t feel fear, but most of us do.

Espree tells us that Lucas and Eliot are doing this show because they feel passionate about being an entrepreneur and they want to share that passion.

There is so much passion, vulnerability, honesty and energy in this interview that you are going to get a lot of value from watching it.

Contact (46:10)

Twitter: @espreedevora and @WeAreLATech

Website: WeAreLATech.com

Tweets

• How about AB testing your life?
• It is never going to be a good day to charge for your product?
• The fear that is part of being an entrepreneur.
• More ability invites your audience and listeners into your own mind and soul.

This week’s interview is with Espree Devora. She is doing amazing work in LA helping startups get off the ground and we talk about one of her specialties: outsourcing.

It is also a landmark episode, because it is the first show with co-host Eliot Peper. Eliot was on the second episode of this show. He is an awesome guy, a great thinker, a lot of fun and he writes startup fiction thrillers. He is about to come out with his second book. Lucas and Eliot have a fiction bond with each other and it goes a lot deeper.

We discuss a book that has really caught my imagination lately: Antifragile: Things That Gain From Disorder by Nassim Nicholas Taleb

I herd of the book before, but after hearing an interview with James Altucher, it really drew me in to finally pick up the book.

Audio Podcast

Here is just the audio for those who are interested in listening:

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Antifragile (6:40)

What’s the opposite of fragile? Many people think it is durable or flexible; like a pair of 15 year old jeans! This is indeed the dictionary meaning, but it is wrong.

Resilient is neutral, but not the opposite of fragile. The opposite of fragile, is something that takes stressors and becomes stronger.

Fragile is like a tea cup: it shatters under stress.

Anti-fragile is like a muscle; where the more you rip it the stronger it grows.

With jobs as well, there are fragile, resilient, and anti-fragile jobs. A sales person is a fragile job because if you insult someone or say the wrong thing you can get fired.

A bouncer may be a resilient job; you can say what you want and you can punch people out and you won’t get fired. It doesn’t help your job or make it better or worse.

There are antifragile jobs that benefit from chaos. An author or artist is an antifraigile job because if you say or do something that gets media attention it may cause you to sell more books.

Small Giants (15:40)

Eliot recommends a book called, Small Giants, by Bo Burlingham.

It focuses an profiles companies that are extremely successful and choose to remain small. They have all had the opportunity to expand but choose not to.

In Indonesia there are tuk tuk drivers. Eliot has been there a number of times. The streets are chaos, it is a war zone, there are industrial trucks driving alongside cyclists and it is a permanent traffic jam.

There are thousands upon thousands of Tuk Tuk drivers yet the one he had was so friendly. He would talk to people, give them treats and just because he focused on the human connection, he ended up having more referrals, that he never had enough time to serve them all.

Eliot can only imagine the lessons he has learned about humanity from building and operating that.

Espree Introduces Herself (20:45)

Espree is excited to be on the show and tells us that there are the most authentic and transparent conversations. Lucas is so real and has no bs, he shares his raw and honest insite with the world.

Espree started being an entrepreneur when she was a teenager. She feels she was born one and did things she liked. She didn’t know she was a producer, entrepreneur or podcaster. Everything she discovered she was really passionate about, she was already doing before she became it.

When she was a teenager she learned a lot of hard lessons. Espree spent tens of thousands of dollars on consultants,raising money or getting an expensive law firm. She thought that it was really cool to have an expensive law firm and the assumption would be to her getting venture capitalist money. She wanted to be the, “google” of action sports.

She made a lot of assumptions that were not accurate that led her to being passionate to moderating panels. Her experience was that she thought there was only one way, but she shows entrepreneurs that there is more than one way.

She feels her intuition is her oricle. She is afraid every day and every day takes a step forward no matter what. She loves moderating panels, connecting people, (although not being paid for it), and the world of startups.

She asked how she could combine all of those things together. When she found podcasting it brought it all together. She found packages of podcasting equipment for ten thousand dollars and realized she didn’t need that. She made that mistake before and bought a $25.00 mic. She uses fiverr to help her as well.

Tim Ferriss has a great podcast: The Tim Ferriss Show.

Time management is a big topic and everyone has a lot to do. If we prioritise our time and group things together we have time for the things that matter to us. All day long we make choice to put yourself in the place that we are in.

Too busy to read? Warren Buffett, is said to spend something like 80% of his time reading and is committed to ongoing learning.

Espree’s Podcast (36:48)

Espree’s podcast is called, WeAreLATech. It his #2 across all categories in Itunes new and noteworthy. She didn’t even know how to look that she was #2 and when she found out she took a bunch of pictures.

She created the podcast because it was an extension of moderating panels. A lot of investers follow ProductHunt and she uploaded someones app she never knew, and they made it to the main page and were able to get investors.

It was so awesome to be able to help with something so simple and make a difference in someones life. On her podcast, people can listen everywhere, and an investor may hear something they are interested in. She sees the podcast as a connector and wants to create exciting episodes.

Espree started with no knowledge and has learned it all. She has spent a lot of time on editing so she can take out all the boring moments. She doesn’t want to waste anyone’s time and just wants to add value.

She was able to meet with Alex Blumberg, who has a podcast called, StartUp. She tells us it is an amazing podcast and he is a master of storytelling. She was able to meet with him and learn about being a good storyteller.

The most valuable thing she has learned from the podcast startup, is that it occupies brain space. She likes that people think about her all week because she is occupying someones brain space in an amazing way. It is far more valuable than email or phone numbers, because it leaves a lasting impression.

Outsourcing her love life (42:40)

Tim Ferris gave a talk about how he outsourced his love life. She thought that was awesome and wanted to give it a try. She viewed dating as a distraction and wanted to focus on her company. Now she is openminded and hired a virtual assistant, who messages people, on behalf of Espree, and reaches out to people.

She does all the leg work, and Espree just shows up for the date. She never seen their picture and is very open minded towards getting to know them. She loves outsourcing her love life, and decided to take it to an extra level. She created a site for facebook using Striking. You can see her page.

She has found it difficult to meet people through all the things that happen to set up dates but she has had great success. She met a man she had an incredible connection with that was in the military but he had to go back. He didn’t want to put a burden on her and didn’t know how long he had to go for. She has taken a break from outsourcing her love life for a while, to focus on her podcast as well as she randomly met someone she is going to see where it goes.

Lucas asked if it could work for others, and she said if you are not fixating on looks, job, cars and money. She looks for integrity, communication, to laugh, ambition, drive, compassion, she is looking for things that are more important and permanent than money. Money can be lost and people’s look age.

How Do Assistants Filter For The Qualities She Needs? (50:00)

Espree tells us that it starts with hiring her team. She looks for the same qualities in the people she hires as the people she dates. They are pretty good at spotting the qualities as we attract what we are.

She has a site she shares about outsourcing your love life.

Espree appreciates and shows gratitude for the people she outsources to. It is really important to her, that everyone knows, behind outsourcing there is a person. She doesn’t feel it takes away jobs, but gives the opportunity for people to work up to a level of high paying jobs.

Please don’t outsource if you are not able to see the person behind.

Fiverr (52:05)

She outsources her audio, artwork, she got her intro done with music laid behind it. She had a video on fiver with epic parque.

She used oDesk before and views them as her teammates. She asks them what their goals are in their life. She helps others find them so they can make additional income.

Lucas uses fiverr for his show notes and will pass on the link. Espree writes her own and it takes over an hour.

Espree credits all of her assistants at the bottom of her show notes. It allows her to have more time to eat healthier, exercise, and get all the things she needs to get done.

Next week we will continue the conversation.

Credit

Audio mastering by Fiverr’s ariacreative

Show notes written by Fiverr’s ginakane

Ryan Orbuch’s not your ordinary teenage kid. Ryan built Finish, an iPhone app used over a million times. It is known as "the to-do list for procrastinators” and was featured #1 in productivity in the app store. 

After he received an Apple Design Award in 2013, it was covered on New York Times, TechCrunch, Forbes, CNET, The Huffington Post, and more. Ryan was also featured on Bloomberg TV and Fox News.

Ryan gave a TED Talk and was hired at Techstars Boulder. He is also deeply passionate about education reform. This week we get into his mind a bit and get to know what makes him tick and what gets him excited.

A few weeks ago, we interviewed online marketing guru Neil Patel. This week I talk to his other half, product guru Hiten Shah. Together they are responsible for epic great tools like KISSMetrics and CrazyEgg, and Hiten's focus is on growth hacking and product engineering... how to create a great product.

Hiten just started a weekly newsletter that covers SaaS topics: SaaS Weekly (http://hiten.com)  that you should totally check out. In the mean time, here's my interview with this great man.

Joanna Penn, NYT Bestselling Indie Author and popular podcaster, has a masters degree in theology from Oxford. Joanna then spent 13 years working in IT consulting. She would implement accounts payable into large corporates. 

Like many cubicle slaves… she was paid well, traveled lots, had what you are “meant to want” in life and was miserable.

She tried everything to get out of IT. Like starting a scuba diving company in New Zealand (which tanked). She did property investing in Australia, which she couldn’t care less about. She tried lots of things and always went back to her day job.

Three years ago she left her day job to become a full time author and professional speaker.

Brand building isn't just for big companies. Any time you are interacting with a customer or user, your are building your brand. If you aren't doing it intentionally, then you are doing it implicitly. Jeremiah Gardner and Brant Cooper just wrote a book The Lean Brand, that gives you step by step instructions for how to build a great brand for yourself or your company. Learn their secrets in this week's podcast.

Learn from a real working venture capitalists in action, why does he invest and what does he invest in?

Always wanted to know why investors go cold sometimes? Find out why in this candid conversation with a professional seed investor and mentor of mine.

Tucker's New Blog: http://www.tuckermax.me Tucker's New Startup: http://bookinabox.co Tucker Max has sold millions of copies of his college humor books and is known for stunts like attempting to donate $500,000 to Planned Parenthood in order to decrease his tax burden and promote his new book. In this episode of the Craftsman Founder Podcast I ask Tucker if any of his past decisions still haunt him. We also go into big ideas like the future of publishing and talk about some disruptive technologies Tucker is working on now. Finally I ask Tucker what the best advice he has ever received is and what common mistakes he sees founders making every day. This is a great episode jam packed with awesome perspective and advice. Don't miss it!

Are you paralyzed with fear of failure and rejection? Or do you have dreams of getting rich with startups? This week is a special episode where instead of Lucas interviewing one of his mentors, you will hear Lucas be interviewed about what it's like to start a company and how to manage yourself through the process. We talk about a little discussed topic of founder psychology and the crazy things that go on inside an entrepreneur's head while starting a business and how to break out of short-term thinking to build more successful businesses. We will also reveal the big secret key behind fundraising, sales, marketing, recruiting, leadership and every other aspect of running a startup.

Neil Patel is an online celebrity and entrepreneur. He has been a prolific blogger on QuickSprout and the KISSmetrics blog since 2006. He has contributed to Entrepreneur Magazine, TechCrunch, Mashable, Business Insider, SEOmoz, and Geekwire. He has also mentored and advised endless numbers of entrepreneurs over the years, including myself.

Neil is a true Craftsman Founder of multiple companies: ACS (SEO), Crazy Egg, KISSmetrics which all have generated many millions of dollars a year in revenue. I am lucky to call him a friend and thrilled

Here is just the audio for those who are interested in listening:

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Show Notes

• Your startups, KISSmetrics and Crazy Egg both use data to tell you stories of how people use your websites. Why is that important? When people build websites, they tend to focus on traffic. A million visitors a month to your site doesn’t guarantee success if those visitors don’t convert into customers. Understanding the entire story path of your users from where they come from to when they buy is critical for long-term success.

• Many decisions are gut instincts and opinions, do you have any examples of how measuring data lead to surprising results? Yes. It is “common knowledge” that you need to reduce friction to get people to sign up, therefore you are supposed to minimize the things you ask a person to tell you up front. For example, you usually don’t ask for the person’s URL during signup. But using data, we found that asking for their URL first actually INCREASES SIGNUPS.

• How did you discover this?

1. Through data–Using Google Analytics, KISSmetrics and Crazy Egg
2. Qualitative feedback–SurveyMonkey, Qualaroo, Promoter.io
3. Peers–We saw other smart people we know trying these ideas

• How does thinking like your customer help you make more sales? Think of a website as a first date. If someone lands on your site, let’s get married is: give me your email, password and credit card… that’s a really tough sell. But if you say: Good to meet you, what’s your name or URL? You start building a relationship with your audience which will make it easier for deeper engagements with your customers.

• How can you use data to piece together the stories about how customers find out about you? Do it in bite sizes. Figure out and optimize just one part of the story at a time. Find where you have the most drop-off to start with. For example, focus just on your homepage. Then focus on your checkout pages. Do it piece by piece.

• What do you do when you don’t know what needs to change?Survey readers (using Qualaroo or Promoter.io) and ask them “what else would they like to see on this page?” Then look for commonalities. Let your visitors tell you where you are wrong.

• What are the top 3 most common mistakes that you see startup founders make?

1. Founders don’t execute fast enough. They want to create the best product or over-thinking things rather than testing and measuring results.
2. Making decisions based on what they want vs. the data. They end up building products nobody wants to use or pay for.
3. They don’t think about marketing. The best product in the world still needs to be marketed. People think they can’t start marketing until they finish the product or feature. These are just excuses and the excuses never ends. You will always come up with more reasons to not start marketing yet. The product does not need to be done to start marketing it.

• You are an expert on online marketing. How can people attract more attention to what they are doing?

1. SEO. Google can drive a ton of traffic to your site. Read The Beginner’s Guide to SEO. Then read The Advanced Guide to SEO. Then focus on link building. Read The Advanced Guide to Link Building and The Backlinko Blog.
2. Content Marketing. Educate people. If you don’t have time to create your own blog, guest post on other people’s blogs. Buffer did this on Forbes and Entrepreneur blog. Read Copyblogger and ProBlogger to learn how to blog effectively. Finally, read The Advanced Guide to Content Marketing.
3. Social Media. To figure out social media, read The Social Media Examiner. Facebook is the second most popular site on the Internet (after Google) so figure it out.

Start from wherever you are and with whatever skill level you are, no matter how bad you think you are. The only way to get better is by practicing and doing things. If you tell yourself that you are bad at marketing or sales or whatever, and you let that be an excuse for ignoring it, you are handicapping yourself unnecessarily.

• What’s the best piece of advice you have ever received about starting a company? Go out there and generate revenue as quickly as possible. It sounds silly and simple, but most people think they need a product before they start charging people. Locking in customers before your product is done really helps change the perception of your business from a consumer or investor standpoint. Without revenue you give up control of your future.

• How has marketing changed in the last few years for startups? Gone from just SEO and paid acquisition to becoming much more creative. Engineers have become much more involved in marketing. Your product can be involved in marketing. Like Dropbox’s invite people to get free credit.

New York Times bestselling author of The Lean Entrepreneur, Patrick Vlaskovits, talks about how to apply lean startup principles to your company to find product-market fit and avoid common mistakes and pitfalls many entrepreneurs fall into. From coming up with startup ideas to evaluating them and marketing them, Patrick brings his wealth of expertise to bear in this great interview.

Many founders hope to one day take their company public on the stock market and have it be worth over $1B+ in market cap. To Dave Hersh, this dream is a reality with Jive Software, a company he founded and lead for 8 years and through 3 different business models.

Dave also happens to be one of my personal mentors and friends. This week we have the honor of interviewing Dave, who runs a brilliant startup blog and often talks about founder's impatience.

I ask Dave many tough and interesting questions this week like:

If you got a Stanford MBA and then worked as an investment banker... what would be your next career move? Michelle Miller decided to write a novel called The Underwriting. But she didn't just write a novel and hope to get traditionally published, she treated her novel as a startup. She raised investment, secured brand sponsorships, created screen savers and playlists, made a video trailer and serialized her novel (a modern Charles Dickens). This week, I interviewed Michelle in the Craftsman Founder Podcast and ask a bunch of questions:

• Tell us about your background
• What is The Underwriting?
• What’s worked and what hasn’t worked well in promoting your novel?
• With your Stanford MBA and then investment banking background, how is writing a novel like doing a startup?
• What can entrepreneurs learn from authors and vise-versa?
• How does an author promote and do marketing for her work today?
• Are you a plotter or a pantser?
• What writing apps do you use?
• Who inspires you?
• Have you considered traditional publishing?
• What attracted you to self-publishing?
• Is fiction a viable investment for venture capitalists?
• Should more fiction authors consider trying to raise venture capital for their novels?
• What do you like best about writing?
• So what’s next for the Underwriting?

Eliot Peper is an entrepreneur, an investor, an advisor… and now an author of startup fiction. His first book, Uncommon Stock (published by Brad Feld’s new publishing company FG Press) at its surface seems like an uncommon next step for most entrepreneurs. However if you treat a novel like a startup, you can understand the decision better. This week, I spend some time interviewing Eliot around a few topics:

• How is writing a novel like doing a startup?
• What can entrepreneurs learn from authors and vise-versa?
• How does an author promote and do marketing for his work?
• Are you a plotter or a pantser?
• What writing apps do you use?
• Who inspires you?
• You were originally going to self-publish?
• What attracted you to self-publishing?
• Was it hard to decide between FG Press and self-publishing?
• Was it harder than you expected to write the book?
• What do you like best about writing?
• What’s next for you?

Chris Tacy is one of my startup mentors and close personal friends. He is not only a brilliant strategist, but he has had 4 successful start experiences in a row with 4 successful exits and no (major) failures. A rare occurrence in startups. He has some surprising advice to share, so find out his secrets.