Hiro Rodriguez has spent a lifetime building mentoring relationships, on both sides of the spectrum. He started as a Cutco rep in San Jose, then was largely developed in the South Coast Division organization while at school at University of San Diego, and for several years after his graduation. After a successful run at Salesforce, he joined the pre-IPO DocuSign “rocket ship.” There, Hiro became Chief of Staff to Chairman/CEO Keith Krach, one of the foremost business leaders in America, from whom he learned many incredible lessons about business and life. He followed to Keith to Washington DC where he served our country as the Chief Business Officer in the US State Department. Now, he has settled into a new role as the Chief Revenue Officer at Prefect, a fast-growing software company.


Q: What were your early days in Cutco like? What were some of the lessons you gained in those early days?

  • Vector was my first job after graduating from High School.
  • I got to work with my friends, which made it fun! We were all super competitive too.
  • I realized I didn’t HAVE to work an hourly job.
  • It was hard work, but it was FUN!

Q: What made you decide to go into management with the company?

  • One of the biggest things Vector gave me was this is unique opportunity, because it gave the value of a personal education.
  • I was so grateful that someone once recommended Dale Carnegie’s book How to Win Friends and Influence People. I just don’t know if I would have had that without Vector, the idea and practice of bettering yourself outside of a formal education.
  • The Vector vibe of a positive attitude.

Q: What were some other experiences during your Cutco/Vector days you would say were transformational in your life or career?

  • PUSH periods. We’d get to learn something unique at team meetings and key staff meetings.  We were taught how to think about goals.
  • Rock climbing example – Whenever you look at a goal and you look to the top it can be daunting, but if you look at just the next ten feet ahead of you and say, I’m just going to get to the next spot, and then the next ten feet, and so on. (Mountain climbing video is by Todd Skinner).
  • I still have my notes from a talk that you gave, “The Power of Choice” that changed my life, and the idea was that you always have to make the harder choice. “Success is defined as making dozens of decisions every day, and always making the harder choice.” – Tom Cannon
  • We’re not just here to learn how to sell a product, that happens to be knives; there are personal development lessons that are universal and transferrable.

Q: How did you get into Salesforce and what was it like working there?

  • I wanted to be closer to home (Bay Area).
  • Cutco buddy introduced me to LinkedIn, where I connected with an old USD buddy who worked at Salesforce.
  • I knew I was bringing my work ethic to Salesforce.

Q: You were recruited to DocuSign by another former Cutco person, how did that unfold?

  • At Salesforce, if you performed well, there was lots of opportunity, things were going well.
  • I was introduced to Mike Arrieta, Vector alum, by another Vector alum Michael Coscetta (also featured on Changing Lives podcast).
  • I had a meeting and met with the CEO, CFO, President, and Head of Sales.
  • It was a tough decision considering I had a comfortable position at Salesforce.
  • Amazing how just knowing one important contact can alter the course of your life.
  • “Every day you’re encountering people who could ultimately change your life.”
  • The importance of relationship building.
  • I had a customer that I met as an 18 year old selling knives, and many years later we reconnected. That connection has now transformed into this guy becoming an advisor and we’re working together to help grow another startup company.

Q: Tell us about your ride through DocuSign. You were there through explosive growth and IPO, tell us about that ride.

  • It was a rocket ship, if someone offers you a seat on a rocket ship, you don’t ask where, you just get on that ship!
  • I worked directly with the CEO and Mike Arrieta I was brought in to focus on bridging the gap between our enterprise sales cycles and our CEO Keith Krach. I was the bridge between the sales organization and Keith.
  • Eventually I became Chief of Staff to Keith. I got to witness strategic chess moves. I got to ask him questions, even ones that relate to my personal life.

Q: What were some of the keys to the growth of DocuSign? What did you observe that other people could learn from?

  • One of the key tenets of the company- “We always hire the best people, especially if they’re better than us.” Always look for A+ candidates.
  • As a leader, this forces you to grow. You always want to be able to give value to your people, and this is why ongoing learning is so important.
  • Life grades concept. Most people stop after their 16th year of formal learning. Continuing our education beyond that allows us to be ahead.
  • Made the commitment to do the 50 book challenge in 2018 (can see list with short thoughts at the end of these show notes).

Q: Recently Keith was named Business Leader of the Year by Harvard Business School, and you had the chance to be his right hand person.  I’d love to gain a little insight in what it was like to work with him, and what qualities he brought to the table as a leader.

  • Keith is into humility and modesty.
  • “There’s no limit to how far a man can go, if he doesn’t mind who gets the credit.”
  • Rule #1 is direct, open, honest communication.
  • There are times for learning how to give AND how to receive good critical feedback.
  • When you keep the doors open to receiving feedback, eventually you’ll get ideas from people that can be life changing.
  • “Diversity of thought is the catalyst to genius.”

Q: What comes to your mind, when I bring up mentorship?

  • I asked Keith, “Who is the greatest leader in your eyes?” Keith replied that it’s not about having one ideal leader, it’s about the Hybrid Leadership Matrix.
  • You can have different people to call on depending on the strengths of characteristics or skills, instead of just one person to call on.
  • “When you’re a parent, you have two jobs: give your kids confidence and give your kids a bunch of different people to look up to.”

Q: Tell us about what you’re going to be doing in Washington, D.C. and how in the world did this unfold for you?

  • I am going to become the Chief Business Officer for the U.S. State Department. I will also be Senior Advisor to the Undersecretary of State for Economic Growth, Energy, and Environment (Keith Krach).
  • My focus will be: “How do we take this huge gap between private and public sector and create a bridge?”
  • I think about how the private sector is about profit, driven by shareholder value. The public sector is about service, how can we impact as many people as possible.  I’ve thought how companies could have a double bottom line.
  • We want to help transform people’s lives and have a positive impact.

Q: How do you want to change people’s lives in the future through your work and through your influence?

  • There’s a value in a mission in creating leaders with opportunities for professional and personal growth.
  • My aspiration in life is to be a positive influence to as many people as possible.
  • You can have the greatest message in the world, but if you don’t have an audience, it doesn’t matter.
  • I don’t know what I’m going to do after this Chief Business Officer for the U.S. State Department, but I’m just going to focus on this next 10 feet.


  • The Power of Choice. There are so many daily choices, typically the easier expedient choice does not lead to any value, whereas the tougher ones do.
  • One connection changed Hiro’s life. Are we bringing our best selves to every day to day interaction?
  • “Diversity of thought is the catalyst to genius”. Are you welcoming diversity of thought into your life? Or are you living in an echo chamber?
  • Hybrid Leadership Matrix. Make a list of what you think are the most important qualities that you aspire to embody in your life.  Who do you think embodies those things at the highest level, each individual quality, not all of them in one person.


  • Key Staff – a group of management candidates on a team who work closely with the manager to learn both sales and personal development skills.
  • PUSH Period or PUSH Contest- typically a 2 week sales contest that allows sales representatives to push themselves and see what they can accomplish in a short amount of time.
  • District Manager- a Cutco/ Vector office manager that runs a year-round office full time.
  • Silver Cup- The trophy award to the #1 rep/ manager in a given competitive category.

HIRO’s 50 BOOKS LIST (Ranked from 50 to 1, with observations on each book)

Tier 3

  1. 12 Rules for Life: An Antidote to Chaos. By: Jordan B. Peterson – Very little lessons of substance that you haven’t heard before and the narrator was a struggle to listen to on audiobook.
  2. Origin: A Novel. By: Dan Brown – I hoped and hoped AND HOPED that this would be as good as Dan Brown’s other famous book, the Da Vinci code. Nope.
  3. The Queen. By: Mikal Gilmore – (Aretha Franklin) – Aretha Franklin is a boss. This book is not. It’s just the story of her journey but nothing truly inspiring comes from this story.
  4. Born a Crime Stories from a South African Childhood. By: Trevor Noah. Trevor Noah is funny but this book doesn’t showcase his comedy as much as I would have liked. But a great story to gain a perspective on apartheid in South Africa.
  5. The Rooster Bar. By: John Grisham – Interesting book especially given last year’s news around the for-profit institutions that totally duped young aspiring students. Interesting ending.
  6. Fahrenheit 451. By: Ray Bradbury – I remember buddies of mine loved this book in grade school so I had to give it a shot. I’m starting to be convinced that I’m not a big fiction book kind of guy.
  7. Finding My Virginity: The New Autobiography. By: Richard Branson – If you’ve read any of Richard Branson’s other books, you know that he prides himself on being a “yes” man. Same story here. Except this one includes a pretty strong Virgin Galactic commercial.
  8. Astrophysics for People in a Hurry. By: Neil deGrasse Tyson – I was in too much of a hurry…
  9. Drive The Surprising Truth About What Motivates Us. By: Daniel H. Pink. I’ve heard so many people talk about this book, I think that my expectations were just too high. There were some interesting points here and there.
  10. The Prince By: Niccolo Machiavelli – There were some interesting stories….ya – that’s all I got. Probably need to give this another try.
  11. How to Own Your Own Mind. By: Napoleon Hill – Napolean Hill’s more popular book, Think and Grow Rich is one of my favorite books of all time. Once again, the bar was set too high and made this one come up short. If you have not read any of his books, I recommend starting with this one and then read Think and Grow Rich.
  12. The Seven Spiritual Laws of Success By: Deepak Chopra – Good ‘ol Deepak. Similar to when I have heard him speak, he shares good advice. But it just did not resonate with me personally.
  13. So Good They Can’t Ignore You. By: Cal Newport – Have you ever have a coach/leader that is more of a hype man than a thoughtful and strategic leader? This book is that hype man. You get fired up for about 2 weeks and then you realize it’s a bit amateurish kind of advice.
  14. Win Forever. By: Pete Carroll – The bar was set too high after reading books by John Wooden, Bill Walsh, Urban Meyer, etc. Sorry Pete. This is a good book but I think I might enjoy your next book when you share the secrets on how you beat my Broncos in Super Bowl 48.
  15. The Captain Class The Hidden Force That Creates the World’s Greatest Teams. By: Sam Walker – I thought I was going to love this. There were certainly a lot of counter-intuitive lessons and surprises that I loved learning about some of the best Captains of our time. It was just too drawn out in my opinion.

Tier 2

  1. The 17th Suspect. By: James Patterson – A good mystery page-turner. Perhaps the fact that it’s just a fun fictional book without much real-life application is why it went down on my list.
  2. The President Is Missing. By: Bill Clinton & James Patterson – I wanted to love this book so badly because I absolutely think the world of Bill Clinton. I just think he’s a better President than he is an author. John Grisham is also one of my favorite fiction authors so perhaps my expectations were set too high.
  3. The Power of Positive Thinking. By: Norman Vincent Peale – Do you want to think positively? Oh – you do? Okay, this is probably worth a read.
  4. The Culture Code The Secrets of Highly Successful Groups. By: Daniel Coyle – If you lead a team, this is a great book to read as you look to scale up and maintain a tight environment. I am looking forward to applying these principles in a big way.
  5. The Happy Vegan A Guide to Living a Long, Healthy, and Successful Life. By: Russell Simmons – After this book and a few other inspiring conversations, my wife and I decided to cut back on meat. However, this is a completely extreme outlook on veganism and in my opinion, extreme viewpoints on anything are rarely a good idea.
  6. The Four Agreements. By: don Miguel Ruiz – If you asked me what the four agreements were right now, I could not tell you. But they were good when I read them! So, it’s a tier 2 book on this list.
  7. The Boys in the Boat. By: Daniel James Brown – This was a well-written [and LONG] book. I thought this was going to carry the same suspense as the book, Unbroken, (which is also a great movie). It’s not. Plus side? Part of the book takes place in the Bay Area so it’s neat to visualize where some of the races happened in the early 20th century.
  8. The Power of Habit. By: Charles Duhigg – This was an ~okay~ book. The concepts were great but nothing mind-blowing that I hadn’t heard before.
  9. Wired to Eat. By: Robb Wolf – Throughout my life, I have enjoyed reading books on leadership, financial smarts, relationships, but rarely have I educated myself on diets (outside of 100’s of Men’s Health magazines). This is a good one if you are interested in learning how your body works with the food you eat.
  10. The Making of a Man. By: Tim Brown – This is a great example of how a man of faith can hold onto his true north while playing in the NFL.
  11. Radical Candor. By: Kim Scott – A great reminder that you will do others a service by having honest feedback and frank conversations.
  12. Quiet Strength. By: Tony Dungy – Talk about trials & tribulations. Getting fired as a head coach, coming back and winning the Super Bowl. And going through the worst pain a person can endure, losing a child at a young age.
  13. What It Takes to Be Number One. By: Vince Lombardi Jr. – When I was little my grandparents gave me a book of quotes from Vince Lombardi. As a child, I started to understand his greatness and it was interesting to hear more from the perspective of his son.
  14. Animal Farm. By: George Orwell – I skipped this one in high school so it felt only right to pick it up again. I usually don’t do too many non-fiction books, as you can see, but I would absolutely recommend this and put it at the top of the [non-fiction] list.
  15. Coach Wooden and Me. By: Kareem Abdul-Jabbar – John Wooden is one of my favorite coaches/authors of all time. Kareem Abdul-Jabar’s perspective is really interesting. If you are a basketball fan, you’ll love learning the origination of the hook shot.

Tier 1

  1. The Five Dysfunctions of a Team. By: Patrick Lencioni – I have had the wonderful privilege to witness some dysfunctional teams. Those are often the teams that you learn the most from.
  2. Hillbilly Elegy: A Memoir of a Family and Culture in Crisis. By J. D. Vance – As someone who has spent the majority of his life on the California coast, this was a very well-written (and easy-to-read) book that helped me understand how many people in this country live on a day-to-day basis.
  3. The Score Takes Care of Itself My Philosophy of Leadership By: Bill Walsh – Growing up in the Bay Area surrounded by 49ers fans, it was very neat to hear the logic behind the West Coast Offense and other ideas behind Bill Walsh’s genius.
  4. The 4-Hour Workweek. By: Timothy Ferriss – Very interesting and practical ideas to increase your productivity in a world where we are always attached and connected to our devices.
  5. The Secret. By: Rhonda Byrne – This was the one book that I have read in the past. It’s just too good not to do a refresh every once in a while. This is easily a top 3 book of mine but it’s lower on this list only because it wasn’t a new adventure relative to all of the other books.
  6. Black Like Me. By: John Howard Griffin – Eye-opening and a great reminder to always be empathetic. The author literally put himself in somebody’s shoes by posing as an African-American and traveling across the South in the late 1950’s.
  7. I Can’t Make This Up Life Lessons. By: Kevin Hart – Pretty funny book. This was the only book I read this year that actually made me laugh out loud. I’m smiling as I write this thinking about one of Kevin Hart’s funny stories.
  8. Above the Line Lessons in Leadership and Life from a Championship Season. By: Urban Meyer – E + R = O (Event + Response = Outcome). Always a good reminder that we may not be able to control our circumstances, but we can control how we respond.
  9. Start with Why How Great Leaders Inspire Everyone to Take Action. By: Simon Sinek – If you have seen Simon Sinek’s famous Ted talk, this is a great companion piece. I highly recommend this book as it really solidifies the concepts of the Golden Circle.
  10. Winners Dream: A Journey from Corner Store to Corner Office. By: Bill McDermott – Bill McDermott (CEO, SAP) is one of the most inspiring CEO’s I’ve had the pleasure of meeting with over the years. His book is a great playbook for any leader.
  11. The Wisdom of Sundays. By: Oprah Winfrey – It’s Oprah – shall I say more? The audiobook and hardcover are different. Both are absolutely amazing in their own right.
  12. The Big Leap By: Gay Hendricks – If you are thinking about making a big change in your life or your professional career, this is a great inspiration.
  13. 41. By: George W. Bush – Coincidentally, I finished this book the week that George H.W. Bush passed away. An amazing tribute and love story by one of my favorite Presidents, George W. Bush.
  14. Red Notice: A True Story of High Finance, Murder, and One Man’s Fight for Justice. By: Bill Browder – I still cannot believe this is [allegedly] a true story and news still comes out on this guy on a frequent basis. Action-packed and suspenseful.
  15. Bad Blood: Secrets and Lies in a Silicon Valley Startup. By: John Carreyrou – If you live in Silicon Valley and work in tech, drop everything you’re doing and read this book. It’s a page-turner and based off of my experience in this wild town, not an exaggeration whatsoever.
  16. The Sympathizer. By: Viet Thanh Nguyen – A Pulitizer prize winner written by a fellow Bellarmine alum (Go Bells). This wins my personal award for best writing, by a country mile.
  17. The Life-Changing Magic of Tidying Up. By: Marie Kondō – The most concrete actionable items came from this book. My wife, Chantel, knows that I am still on my tidying-up journey but I sure am much improved.
  18. The Five Love Languages. By: Gary Chapman – This is one of the books, similar to Dave Ramsey’s, Total Money Makeover, that will have a lasting and tangible impact on my life. I can already see a powerful difference in my marriage.
  19. Promise Me, Dad A Year of Hope, Hardship, and Purpose. By: Joe Biden – The 2nd book to make me cry. No matter your political viewpoints, I highly recommend this book.
  20. Coming Back Stronger: Unleashing the Hidden Power of Adversity. By: Drew Brees – This was my final and most impactful book of 2018. Drew Brees’ book is a constant reminder to hold onto a positive attitude, embrace adversity, and keep the faith that something bigger is planned for your life despite temporary setbacks.

 2 key books mentioned that Hiro read outside of the year 2018:

  • Mindset by Carol Dweck
  • Multipliers by Liz Wiseman


Show Notes for this episode provided by Brian Njenga.

To learn more and get access to all episodes, visit our podcast page!


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