Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business

by Maynard Webb, Carlye Adler

The Los Angeles Times and USA Today bestseller!

Wise, practical, and profitable letters to entrepreneurs, leaders, managers, and business owners in every field―from a leading executive, investor, and business founder

More than 600,000 new businesses are launched each year. How can a start-up find the funding it needs to survive? When, if at all, should a company go public? How does an entrepreneur build and manage a workplace―and create a lasting legacy?

Maynard Webb has helped found, fund, and grow dozens of successful companies, and has driven strategic change at Salesforce, eBay, Everwise, and Visa, among other worldwide corporations. Known for offering savvy insight, encouragement, and a dose of reality in the form of engaging personal letters to a select group of business leaders, Webb now shares his lessons with the rest of America’s aspiring entrepreneurs―at any age and stage in their careers―in Dear Founder.

Featuring more than eighty inspiring, informative, and instructive letters, Dear Founder is rich with sound advice on an array of business topics, from turning your idea into a reality to building a culture, to reaching key financial goals. This book is an indispensable guide to navigating the realities, risks, and rewards of being your own boss―and founding the company of your dreams.

Genres: Business, Leadership, Startup, Entrepreneurship, Management, Nonfiction

352 pages, Hardcover

Published September 11, 2018

Reviews

[Cindy · Rating 4 out of 5]

Every early stage founder should have this book on their bookshelf as it is an excellent reference manual as you encounter the wild assortment of issues facing startup founders, many of which you may not have seen before.

Choosing to write each piece of advice as a letter was innovative and I appreciate the brevity of each letter. Unfortunately that means some of the advice may appear more simplistic or superficial than one may want; however, minimally each will help you figure out the questions you need to answer to resolve the challenge at hand. Oh how much fun it would be to have lunch with this author!

Thank you to NetGalley and the publisher for providing me with an early release in exchange for an honest review.

[Jason Orthman · Rating 4 out of 5]

Really good book on leadership from a tech industry veteran. Transparency and communication is crucial.

[Sebastian · Rating 3 out of 5]

This is a pretty good business book. Maynard Webb, who was COO of eBay under Meg Whitman and later CEO of LiveOps and a bunch of other operating roles plays spiritual uncle (or more accurately, Polonius to your Laertes) to startup founders and would-be start up founders with a series of letters with bits of advice and inspiration.

It's well-organized into sections corresponding to the lifecycle of a company: (1) getting started; (2) finding product/market fit and building a team; (3) growing and hitting challenges as you go; (4) leaving a legacy. Contrast to The Hard Thing About Hard Things which has some cool stories but can feel like a swirling mess.

Under each section there is probably something that you will find useful. Each letter is conveying some very practical wisdom:
- How to incentivize a sales team (89-91) -- it's not rocket science, but there's some good guidelines on quotas and bonuses if you've not done this before.
-In a section about poor performers "When you need to deal with poor performs" he slips in something very wise: "In our efforts to get the most out of employees we too often make a common mistake: We spend too much time worrying about poor performers and not enough time focusing on the best and the brightest. The real secret to making the biggest impact rests in investing in your best performers and ensuring the become even better" (162). At Palantir managers would put extra attention on thinking about the top 20% of reports and how to accelerate their growth... not that you don't care about the rest, but that you certainly want to make sure the best and brightest are on the steepest possible growth trajectory. "Find a busy person and try to break them" (162).
- Nice meditation on boldness versus hubris (187-191). I think we all like a founder who has strong conviction around a specific plan of attack, but hubris is when you disregard problems or don't mention the sticky bits, boldness is when you have strong opinions about strategy but you also show vulnerability and are thoughtful and seek input and listen to outside advice.
- Build explicit time in your schedule to work on "Important / Not Urgent" problems (250) like painting a vision, inspiring a team, writing blog posts, etc. These are important but because they can require a lot of work and reflection and will never quite blow up in your face if you don't do them, it's easy to ignore them.

Would I recommend over High Output Management? HOM is more focused on, well, management, and so is a bit less comprehensive and also kind of dated. I'd consider this in a package along with HOM and Venture Deals as a good foundation.

[Dora Okeyo · Rating 5 out of 5]

I love this book! If there's one book that's going to be handed down to generations to come in my home library, it's this one.
If you're starting up a venture, a business, or you are an investor, manager and even if your wheels are turning about starting out a venture, this book will not only inspire you, it'll guide you along the way. Thank you Netgalley and the Publisher for the eARC.

[Luna · Rating 4 out of 5]

the author has put the hard works into easy-to-read content, covering all the stages a company could have experience from startup.

A book talking about what would a company experience from a start-up to (hopefully) becoming a legacy.
It provides ideas and solutions to all issues that might occur in all stages.

Though it’s very shallow, it’s easy to read, and it covers all topics.
It’s interesting when I read the letters about what my company has already experienced;
It’s also very valuable to know the ones that haven’t happened yet.
It’s like having a peek of what will happen, and trying to (but will never be able to) be prepared for them.

I wish though,
I wish I will be able to experience all the opportunities and issues that have been mentioned in the letters.
Good and bad, I know it’s only going to be intense, but I know that’s what a successful road looks like.
Dream big. I am dreaming big for my career, and my company’s future.

Hard-working is not the only key, but it’s something essential.
I will try my best to do what I can and then hope for the best to happen.
#dearfounder

[Raimundo · Rating 5 out of 5]

Dear Founder is Maynard Webb's delightful second book. I didn't expect to enjoy it as much as I did. Each chapter engaging and easy to follow, dealing with a common challenge along the founders journey. It's a refreshing reminder that you're not alone in the journey and the universality of so many of the challenges. It makes what is a very hard thing seem far more tractable and accessible, hard but not impossible. I highly recommend, even if you're not a founder or consider being one. Many of the chapters are much more broadly relevant and accessible (for example, "when you need to recruit" or "when you need to build a workplace of inclusion".

[Kevin Leung · Rating 3 out of 5]

This book is not meant to be read cover-to-cover. Despite that fact, I more or less tried to read it cover-to-cover, though I had several large gaps and stops in-between.

It’s hard to rate this book because it’s intended to be used situationally when you need advice on a certain issue. I imagine that each roughly 2 or 3 page letter is more or less what Maynard would say to you if you admaked his advice on a situation.

I didn’t particularly pick out notable takeaways, but maybe I just don’t need this book right now. Should I find myself in a pickle, though, I will probably reach for it in addition to other resources.

[Dominik · Rating 1 out of 5]

Not useful at all.

[Martynas Petkevičius · Rating 1 out of 5]

I rarely consider business or management books useful or interesting, but Dear Founder has hit an all-time low. It's supposed to give you advice on how to deal with situations commonly faced by start-up founders, but instead it just lists things to consider. For instance, when talking about raising funding, Webb casually mentions the importance of understanding terms like cap, pro rata and liquidation preference, but never explains them. Similarly, the chapter titled "When you need to focus on what's important" simply rewords the title by stating that you need to focus on important and / or urgent tasks as if it was some kind of a revelation but doesn't actually tell what IS important.

The whole division of the book into letters is a total gimmick, restricting itself to the greeting "Dear Founder" and closing "All the best" with a fake signature attached. You're supposed to read the relevant letter when a problem arises, but seriously, when would be a good time to read a letter called "When you you want to avoid nasty surprises"? When wouldn't you want to avoid them?

Thankfully "Dear Founder" is a very short book, printed in decently-sized font, with thick margins and noticeably large line spacing. I imagine even all that spacing and fluff wasn't enough fill 300 or so pages to make it publishing-worthy, so the editor was compelled to also start every 2-4 page long letter on a new page, sometimes leaving just two lines on the previous one. It's funny, because it reminds me of how I employed similar tactics in school to make my essays look longer.

Some books like Gladwell's Outliers present ungrounded, but fascinating ideas in engaging prose. Others, like The Business Book of Big Ideas Simply Explained series lack in style, but at least provide comprehensive coverage of various business concepts. And then there are books like Dear Founder which have neither form, nor substance.

[RJ · Rating 4 out of 5]

Maynard Webb’s Dear Founder is a different kind of startup story, told through the letters an active investor might share with a founder struggling, failing, persisting, and triumphing in their quest to build a sustainable business. It isn’t a retrospective history of the latest tech IPO, nor fawning Silicon Valley hero-worship—just candid, objective insight into the moments that can make or break a fledgling venture.

The letters are each written for moments ranging from the good (“When you have a big payday”) to the bad (“When your board is driving you crazy”) and the likely terminal (“When your idea just isn’t working”). There are numbers to hit, of course, but also relationships to manage, crises to navigate, and emotions to mediate as things work out—or don’t.

Each letter contains thoughtful, clear, and appropriately generic suggestions, framing complex situations without prescribing solutions. Webb’s considerable experience as both a founder and investor is certainly on display, but with plenty of room left for the reader to tailor it to her own situation.

If the letters have a recurring theme, it’s the collective investment in a successful business. Webb clearly cares for his reader and their team, but the flinty executive is never far away. When tensions arise between star employees and the needs of the team, or between founders’ ideals and investors’ returns, it’s the business that ultimately matters. There are no villains: just finite resources, tough choices, and consequences that may or may not be as consequential as they first seem.

Nor are there heroes. Silicon Valley’s biggest names and fastest rocketships are notably absent. We meet a few of Webb’s colleagues, but the book’s real protagonist is the reader—not one of Webb’s golfing buddies, the founder of his brightest portfolio company, or even the author himself. It’s a humble departure from business-as-usual in startup nonfiction, but it certainly isn’t a change for the worse.

Dear Founder won’t be a book for everyone. Most of us won’t start our own companies or take venture money. But for those that do—or for family, friends, and employees trying to empathize with their journey—this is a worthwhile collection of sincere, uniquely-informed advice.


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Original review on rjzaworski.com.

[Emanuel Vass · Rating 5 out of 5]

If you’re starting a company, own a company, or even work(!) for a company – it’s important not to make preventable mistakes. And that’s what Dear Founder is at its core: a way of avoiding potential catastrophes by addressing them, using the wisdom of one of the world’s greatest businessmen. Maynard teaches everything from how to begin a company, how to fund a company, who to hire, who to fire, how to deal with crises: how to promote, compensate, give feedback to, and lead your team: how to deal with competitors, exits, lawsuits, scaling, and organizational challenges. This book is arguably the most efficiently written and therefore comprehensive manuals on business ever created. It’s an MBA in a book. Enjoy.

[Dalin · Rating 4 out of 5]

I gave this book 4 stars because it reaffirms what I already know about business. When you grew up in a household full of members who do business, it’s hard not to know about it. When you face challenges every day, you also learn every day.

The one star that I didn’t give to this book is because it offers no insight for more, and I’m sure it’s targeted readers want to know more than what they already do. And instead, we’re stuck with the same pieces of advice we already learned when we were teenagers. My father’s advice even came up with his own tales! So thanks, but no thanks.

[Wairimu · Rating 5 out of 5]

Maynard covers every aspect of starting a company ; from conception of the idea, picking co-founders, hiring, fundraising, operational excellence, to scaling. The advise is in very brief letters but covers the topics quite broadly. While the focus of the book is more towards founders, this is very enlightening to people solely in leadership, especially if quite new to leadership. It not only guides you on the day to day mangement but gives perspective on company decisions and other stakeholders roles.

[Matt Brown · Rating 3 out of 5]

As the intro of the book says 'this isn't intended to be read cover to cover but act as guide when you need it'. I read it cover to cover but would reccomend having it as a guide. Some of the topics are pretty superficial and would appreciate more cases, examples, rather than just a high level "you aren't in this alone".

[Dave Applegate · Rating 3 out of 5]

Very short, well worded letters to startup founders. Webb did a stellar job thinking through the topics and making them easy to find / digest. I know this sounds simple, but it's shocking how much startup advice is poorly organized. E.x. Webb doesn't have a chapter on leadership. He has a chapter on hiring a key employee, solving a key employee's engagement issues, firing somebody, etc.

[Rafid · Rating 5 out of 5]

This book is like a bible for founders. I love the way Maynard chose to structure the book into letters that convey a single message. It is very effective and easy to follow. A must read for any founder. I know I will be reading this book several times!

[Hallie · Rating 3 out of 5]

Sound, practical advice from someone who has clearly had a broad range of experience in starting up and managing companies. Certainly applicable to start-up founders, but plenty of applicable advice for those leading teams and working in larger established companies as well.

[Steven J. · Rating 3 out of 5]

This one covers some of the common considerarions and risks for creating a start-up. The topic is probably one that can be written aboout for a series of 10 books. This one is worth a look and read but is limited in scope in today's fast changing landscape.

[Alfredo Salkeld · Rating 4 out of 5]

It’s not the type of book you can read cover to cover, but I enjoyed skimming the well-organized table of contents in search of letters that apply to me. I read a dozen or so. Webb is the real deal. I borrowed this book from the library but may buy a copy to have on hand for reference.

[Sumeet Mahendra · Rating 4 out of 5]

Some very valuable teachings. A sort of must read for every #Founder & #Entrepreneurs

[Greg Kaplan · Rating 4 out of 5]

I borrowed it from the library and will now buy it to keep as a reference. It’s written in simple nuggets (letters to founders) about each stage of growth.

[Fatima-Zahra I’ltaf · Rating 5 out of 5]

Just wow 🤩

[Nancy Tu · Rating 4 out of 5]

這本書除了能在創業的路上帶給我們諸多的啟發之外，非創業人士在工作、管理，甚至是個人生活職涯規劃上都能從書中得到不同的感想和看法

[Kosala Heengama · Rating 4 out of 5]

This book is great for a entrepreneur. It gives advise on mostly all aspects of business life cycle and provides insight on how to address challenges. You can also use some the topic to refer back.

[Erik Britt-Webb · Rating 4 out of 5]

Highly recommended for perspective on this TO DO and NOT to do during different stages of the journey of a start-up business

[Dennies Chung · Rating 4 out of 5]

This book was fantastic. I thought the author - Maynard Webb - had an interesting way of telling the story of his career and how he wanted to visualize his advice to the reader: in the form of letters! The content was easily digestible as the chapter (or letters) were an average of 5 pages each and no more than 20 pages. Innumerable pieces of wisdom from the former COO of eBay, CEO of LiveOps, and board member of Salesforce. I definitely thought that some letters could be consolidated into one single one as I thought the content got a little repetitive at the end, but nonetheless, a great read for any future entrepreneurs, managers, or business founder!

I also wanted to point out and really reiterate that I love the structure and format of this book. Writing is so much more than just storytelling, grammar, etc. It's also a visual art and practice. It's up to the author on how he/she wants to tell the story, and formatting/structuring the words/letters on the page is one mean/method to grab the reader's attention. Kudos on a job well done on the book.

Update 08/12:
I was going through some reviews that I wrote and I feel like I may not have done this book justice on my review. I think this book is valuable and instrumental to any business leader's success. What may seem like common sense in this book to one person may not come as easily to another. The book serves as a great refresher for anyone leading an organization and may even give a different perspective on how to handle different situations.

[My BookSwap Club · Rating 3 out of 5]

This is a must read book for anyone who has founded a company, and are now expanding..or the company is growing (sooner than they expected). It will be like a free consulting advise!

I just read for pleasure and found some areas to be not relevant nevertheless those answers were interesting. I also loved the 'letter' concept It doesn't feel like you are reading a one big business book!

Advise is simple, and easy to follow!

If you are an entrepreneur, looking to grow or are expanding your business - this is a MUST READ for you!