My 25 Favorite Podcast Episodes on Startup & Business Strategy

Paul Graham: Before the Startup, by How To Start A Startup.

[ITunes] [Overcast]

Y Combinator founder Paul Graham gives this superb talk on the reality of startup life, when you should take the leap, who to bring on the team, how to come up with ideas, which ideas are worth pursuing, what he looks for in a company, and more. If you're considering starting a new venture, or are mildly curious, you'll enjoy this entertaining talk.


Chris Sacca: Being Different and Making Billions, by The Tim Ferris Show

[ITunes] [Overcast]

I've heard a few interviews with Chris Sacca before, but this has to be the best of them all. There's so much raw insight in this episode. He's had a bunch of ups and downs in his life but what ultimately put him on top was that despite everything that transpired (including blowing millions in his trading account and being deep in the hole), he saw his success as inevitable. In fact, if a founder lacks that quality, he won't fund the company. In this episode you'll hear about common qualities of successful founders, how he passed on Dropbox and Airbnb, how you shouldn't conflate a good outcome with a good process, who inspired him the most in history, and how he carefully selected his relationships to nurture even before he was established.


When to Quit: Lessons from World-Class Entrepreneurs, Investors, Authors, and More, by The Tim Ferris Show

[iTunes] [Overcast]

I've often wondered how to determine whether it's time to quit something or to persevere. In this episode, Tim Ferris asks the question to six people who've figured that out for themselves. I found my answer in Chase Jarvis' rubric, which was based on asking yourself two questions: 1. whether it brings you joy and is still working; and 2. whether you still care in the mission to willingly endure the difficulties. If the answer to both is yes, then soldier on. Seth Godin's answer was also very helpful in distinguishing between a dip and a dead-end, as was Scott Belsky's response on needing conviction in the mission. The thoughts shared here are relevant to all aspects of life and well worth learning from.


Boeing Vice Chairman Ray Conner: Courage, Servant Leadership, Imagery, by Finding Mastery

[iTunes] [Overcast]

This conversation really stood out to me. Ray rose from being a college drop-out mechanic on the Boeing factory floor to becoming the company's CEO and Vice Chairman. Clearly not the conventional linear path and, as you'll hear, it required some deep inner transformation. Turns out, early in his life he lacked a lot of confidence and courage, however, he managed to flip that weakness into his greatest strength. Much of that was the result of really targeted goal setting, using imagery, self-affirmations and daily self-assessments - all of which he describes in detail during this interview. It's a powerful story from someone who has tenaciously climbed quite a few rungs on the ladder of self mastery.


The Business of Building Wealth by Bulletproof Radio

 [iTunes] [Overcast]

This episode is a must listen. I love a great turnaround story and this one is all about reinvention and developing yourself. The lessons here apply to your business, career and personal life. There is so much to learn from this episode that I'm struggling to summarize my two pages of notes. David Osborn was forced to reinvent himself in his 30s after some struggles. The reinvention was centered on having integrity with himself, his work and with others. He has since built a real estate agency empire with 4,500 agents and has $8.5B in revenues. He's founded 50 companies, 25 of which are profitable. None of that success came easy, but in listening to his story you'll see how through inner transformation, the outer simply flowed. A few of my favorite parts include how life is autobiographical (it is a direct reflection of who you are), how you need to be ruthlessly honest with yourself, that if you're not purposeful in your actions then the agendas of other people will dominate your life, and (my favorite) that if you want to attract great people, you need to be a great person. This episode is electric.


Anatomy of a Theranos Takedown by The Exchange

[iTunes] [Overcast]

This episode has the inside scoop on the Theranos takedown. I've been following the story for a while but there were some interesting anecdotes in this show. For example, how Holmes was obsessed with Steve Jobs and modelled herself after him - she ordered a bunch of black turtlenecks to dress the way he did, and even hired the same ad agency that Apple used for its campaigns. I guess she forgot the part about building a product that actually works. It was also fascinating to see how some well-known and sophisticated investors were able to get duped by her pitches, and why she stacked the company's board with former statesmen (eg. Henry Kissinger) and military officials. Now that it has been exposed as a fraud, the workplace stories have come out and it seems like it was a pretty hostile environment. Whenever the culture of a company is centered on threats and intimidation, it's probably a good reason to look under the hood.


Andrew Chen: General Partner at Andreessen Horowitz, by Inside Intercom

[iTunes] [Overcast]

I liked this interview with Andrew Chen of Andreessen Horowitz a lot. I didn't realize that he came to the Valley about 10 years ago without much of a tech background or network. He started writing about everything he was learning, despite being told he was crazy for giving away his competitive advantage. Thankfully, he listened to his gut and persevered because soon after Marc Andreessen emailed him and the wild tech ride began. He shares some interesting details about some of the companies he's worked and invested in, including Dropbox which he sees as part of a whole new tidal wave of companies that understand the relationship between people (others in that cohort include Slack, Intercom etc). There are also some good lessons here on growth:  the spammy viralty of early social/mobile days are over, and growth teams have to stay ahead. What works now won't work tomorrow, and by the time you read a tactic on Medium, it's probably done. You have to move beyond that to develop frontier skillsets.


Mike Zapata – The Darkest Night: Lessons from Battle and Value Investing, by Invest like the Best

[iTunes] [Overcast]

This is a great interview with a former member of SEAL Team 6 who, since leaving the Navy, attended Columbia business school and has become a value investor. He shares the lessons from his career as a SEAL and how those apply in investing, for example, how preparation is one of the most important methods to de-risk an investment, and how investors need patience to wait for the 'dark moonless night' before putting on a position. He discusses what he looks for in a business, how he measures the integrity of management, and how management's incentives need to be aligned with specific milestones. He also goes into some detail about the 'smoke and fire' he looks for in a struggling company, his blind spots and how he tries to root them out, and how ego is the ultimate risk factor for any investor.


Ask Better Questions by HBR Ideacast 

[iTunes] [Overcast]

As the title suggests, this episode teaches you how to ask better questions. My favorite lesson was on how to pose a question when you suspect someone is lying. Turns out, asking the question with a pessimistic assumption can result in a more revealing answer. They also discuss when to use open or closed questions, the benefit of posing follow up questions, and how to ask questions in a group context with dominant personalities. Although most of the discussion is on the asking of questions, they also address how to answer them better, the role preparation plays, and how to dodge and deflect.


Peloton's Ride to the Top: John Foley, by Been There. Built That

[iTunes] [Overcast]

Every time I walk into a Peloton store, I wish that I enjoyed spinning so I could justify buying that bike. They have such a well-packaged value proposition, from the hardware, software, live workouts, on-demand workouts, and the social-layer woven throughout. So when I saw this episode with Peloton founder/CEO John Foley, I had to listen. His story is far from linear and involved years of grinding away despite a towering-wall of rejection (he had 400 VCs turn him down… 400!). In this interview, he shares how he came up with the idea, how raising money for Peloton was the hardest thing he ever did, that he considered moving into his in-laws basement with his family if it failed, and how he was almost fired by the board because he was too forthcoming about his fears. Clearly, the company is over the hump now with over 1 million people riding, have surpassed unicorn status, and have raised over $450 million. I have deep respect for founders like John that persevere through such storms.


Reed Hastings: Building a Streaming Empire, on Greymatter

[iTunes] [Overcast]

Another founder I admire is Netflix's Reed Hastings. This interview goes deep into the company's culture and how they manage to not manage their employees. Reed explains that the path to get there involved creating a context of accepted behavior and norms in which employees could operate freely. It's a stark contrast to how most companies are run. I was also impressed with how much the company relies on instincts and intuition to make decisions around such things as hiring and creating original content - especially since they are a data driven company. Lastly, Reed offers a terrific lesson on how to react when attacked by a competitor. He shares how none of their counter-attacks actually had any impact on Blockbuster and that after Netflix won, they shut them all down. What he wished he had done differently was to double down on their core competency rather than get distracted with additional features. Going from 98% perfection to 99% would have knocked Blockbuster out quicker than their actual approach. Reed is such an impressive individual that it's no wonder the company has reached such heights.


Crashing is Success by Inside Skunk Works 

[iTunes] [Overcast]

There's a great podcast that's come out recently by Skunk Works - yes, that same Skunk Works that designed the Blackbird, the F117 stealth fighter and a bunch of other stuff we'll never know exists. This episode is all about our relationships with risk and how Skunk Works has institutionalized the acceptance of risk and failure. They share how without risk, products evolve too slowly. Taking risks is how you jump multiple rungs on the ladder. There's also a great discussion on how, once you take a risk, you have to be ready for whatever outcome materializes since nobody actually knows what the outcome of any action will be. That requires a mindset that accepts failure as a very real possibility. You need a cool head that is free from accusatory scapegoating, and is open, inquisitive and focused on learning. Skunk Works takes this form of thinking so far that they have built planes which they knew all along would crash, because in that moment of failure lay the next piece of knowledge they wanted to learn.


Ring CEO Jamie Siminoff on Danny in the Valley

[iTunes] [Overcast]

Jamie Siminoff is the founder and CEO of Ring (the smartphone integrated doorbell camera), which was recently acquired by Amazon for a tidy $1 billion. Jamie is one of the most likeable people in tech and his lack of pretense in sharing the ups and downs of his journey makes this interview such a good listen. The episode dates back to 2017, before Amazon acquired the company, but that made it all the more interesting because he describes the company's vision as being very much like Bezos. It seems like fate came knocking. Jamie shares a lot of stories from the trenches, including how he came up with the idea, how they almost faced bankruptcy, the impact Shark Tank had on sales, how Mark Cuban dismissed the opportunity, and how Richard Branson saw it. However, the most interesting lesson I learned was about the metric by which the company measures its success. Customer acquisition, revenue, etc. were not their primary focus. Rather, they kept a close watch on neighborhood crime statistics. In fact, they don't even see themselves as a tech company but a crime prevention company. That subtle shift makes all the difference in the customer experience because it forces the entire team to be focused on solving their customer's most pressing concern when buying their product - which is crime. Enjoy this inspirational and candid chat with a founder who just gets it.


How to Systematize Your Life for Success: The Less Doing Podcast

[iTunes] [Overcast]

Geoff Blades was a dissatisfied Goldman Sachs employee who went on his journey to discover what he really wanted to do. This episode is full of the lessons he learned and now teaches to his clients. Geoff has come to understand that most people are in jobs they don't want to be in. They don't really succeed because they're not loving it and are therefore lacking the energy required to be the best they can be. They're also not serious enough to leave and do what they truly want. Geoff shares a five-step formula to systematize the migration out of that trap and overcome what holds people back - i.e., the unwillingness to work through fear and uncertainty. This one is a good kick in the pants.


Privacy & Transparency: Benedict Evans, by Thomson Reuters Answers

[iTunes] [Overcast]

Benedict Evans is one of the smartest minds in Silicon Valley. I highly recommend his weekly newsletter. Given his perch at Andreessen Horowitz, Benedict is fortunate to be able to see tech trends forming well before they start getting traction. Much of the discussion here focuses on developments in artificial intelligence and machine learning. I thought it was interesting how believes that Google could not have released Google Home without Amazon's Echo first opening the door - that theory being based almost solely on our perceptions of the two companies. He also has some great insights into the limits of AI and that we need to understand that it's just a machine. I'm glad he said that because the narrative around AI right now has a cloud fear hovering over it.


Five Questions with… Benedict Evans on Danny in the Valley

[iTunes] [Overcast]

As you've probably gathered, in this episode Danny asks five questions to Benedict. They are on 1. self driving cars; 2. crypto; 3. big tech; 4. march of the machines; 5. the next revolutionary tech. I'm going to let him unpack the answers, but it's a terrific discussion you won't want to miss.


Brian Moran: Why Goals Don’t Work, by Entreleadership

[iTunes] [Overcast]

In the past I've been guilty of committing the cliche of setting New Year's goals and forgetting about them by mid-January. So I like how Brian structures goals around execution. He advises setting a long-term vision around 3-5 years out, breaking those down quarterly and then setting actions for each week. The key is have a long-term objective but make smaller adjustments more frequently. It's almost like taking the lean startup methodology and applying it to your personal and career objectives. He also talks about how life-balance is a misnomer. Instead, there are different seasons in life and we need to be ok with giving more weight to certain priorities at different times. That was relief to me since I always feel like I'm behind on something.


Jeni Britton Bauer: Life As A Trailblazer, by 33 Voices

[iTunes] [Overcast]

My friend Jenna hosts this outstanding podcast, and in this episode she interviews Jeni from Jeni's Ice Cream. I couldn't resist listening to it... just as I can't resist their ice cream. Anyone who has been inside their store knows what I'm talking about. This episode is packed with lessons, including how to reinvent a business after a crisis (they went through a painful one), and the futility of trying to be the best, which is ultimately just chasing someone else's past glory. Instead, strive to be better today than yesterday. Another great lesson was on the importance of curiosity and asking questions. In that quest, you eventually discover that there's nobody left to answer your questions, at which point you have become the trailblazer. I also loved hearing how she uses intuition (and trains her staff to use that too) to read her customer's energy and emotion as they wait in line.


Sam Altman and Reid Hoffman: From Startup to Scaling, by Y Combinator

[iTunes] [Overcast]

I never get bored listening to these guys talk startups and tech. They have seen so many companies that they are acutely aware of what helps startups scale. Some key takeaways include, firstly, that you should expect internal and external chaos when scaling and so should condition the company for it. Don't try to manage it out. Secondly, founders who were great running a small team may not be the best at running a larger company. Thirdly, don't hire from a 'resume', instead hire people that can learn quickly and can constantly adjust. In fact, their hierarchy of who to hire is first values, then experience, then skills. Lastly, early stage companies should only hire generalists (especially those that are great problem solvers), and add specialists once the company is well established.


How to Love Criticism: WorkLife with Adam Grant

[iTunes] [Overcast]

This podcast has become one of my favorite new shows and this episode seems relevant since who likes criticism? Well, not surprisingly, mega hedge fund manager Ray Dalio of Bridgewater thrives on it (I'll share an episode on that super deep guy in a future email). Giving and receiving criticism has been a secret sauce at the firm and he demonstrates how they deal with it, how they approach failure and what it can teach us about humility. Adam shares with us the importance of support networks, but that we could also all benefit from a 'challenge network' made up of trusted people who tell us what we need to hear to improve (rather than simply what we want to hear). As an unrelated aside, there's a Bonobos ad that runs during the episode. I normally skip ads but this one was genius in how it engages us with a story. Brands should really be focusing more on making ads like this that give value to the audience, rather than just selling a product. That's the only way to beat the skip forward button.


Nikhil Kalghatgi's, by Invest Like the Best

[iTunes] [Overcast]

This episode is so good. Nikhil is an investor that specializes in moonshot projects, ie, crazy stuff like asteroid mining. He looks out onto the horizon and finds markets that will have explosive growth over the next 3-5 years. Obviously crypto is one of those markets and he's heavily involved in that - not like a 2017 drunken crypto-bro hodling his coins, but with sound and sensible analysis. Nikhil is a funny guy and also teaches a class on humor. In fact, he founded something called 'The Happiness Project' where he interviews some of the most successful people of our time about happiness. But you'll have to listen to this episode if you want to know their secrets.


Thomas Edison's Formula for Success: The Tim Ferris Show

[iTunes] [Overcast]

I would recommend listening to this short episode from where Ryan Holiday reads a chapter from his book, The Obstacle is the Way (one of my favorite books of all time). It opens with one of the greatest lessons on failure and success as taught by Thomas Edison. It's applicable to everyone and is so incredibly good. It starts about 8 minutes into the episode if you want to skip the intro. Give yourself a gift this weekend and listen to this.


SoftBank, Fortress and the Vision Fund, by Acquired

 [iTunes] [Overcast]

Most of you in tech are probably quite familiar with Japan's SoftBank, whose Vision Fund is the largest fund in history (an eye-watering US$93B). We've seen them airdrop billions into companies like Uber, but I didn't know the story of how they got started. This episode profiles the remarkable founder, Masayoshi Son, who started out in the 1950s in a small fishing village in southern Japan but ascended to such heights that he almost snatched Bill Gates's title as the world's richest man during the tech bubble. Along with that achievement, however, he also won the crown for losing the most money in history when the tech bubble burst (somewhere in the order of $77B was wiped off his books). That stomach punch would knock out most of us mortals, but not Masayoshi Son. He strategically rebuilt his empire over the last two decades and is now back at the top of the ladder.


Netflix v Blockbuster: Business Wars

[iTunes] [Overcast]

This show is an outstanding case study of the innovator’s dilemma. They take you right inside the battle between those two companies. I knew the general story already, but some of the details in this corporate bloodsport were new to me, for example, how Blockbuster sent spies into Netflix's distribution centers, how they lampooned the other side during earnings calls, etc. I ended up binge listening to the whole thing in one go while I was finishing off my taxes (which made the whole process that much less mind-numbing).


A Moat Too Far, by Exponent

[iTunes] [Overcast]

When it comes to our day-to-day lives, Amazon has become one of the most innovative companies we engage with on a daily basis. This episode from a couple of months back by Exponent is exceptionally good in discussing the impact Amazon is having on e-commerce (spoiler: it's eating all of it alive), how (if?) companies can position themselves, whether anti-trust is a realistic option, the company's plans with Amazon Go and more. What Apple did with the iPhone, Amazon is doing across multiple industries - at the same time. This is well worth the listen.