Paul Inouye

Paul Inouye

November 8, 2021

Paul Inouye not compromising or accepting a counterparty’s deal and taking your time, and being patient to make the best deal.

Paul Inouye was born in San Francisco and grew up in San Carlos, and is one of three brothers.

Paul Inouye attended Bellarmine College Prep in San Jose, UC Berkeley, and The Wharton School at the University of Pennsylvania for my MBA.

His hobbies include cycling, running, swimming, Crossfit exercise, travel, skiing, 80s music, EDM, 80’s movies, reading, military history, and fantasy football.

Paul Inouye played both high school and collegiate Rugby and has completed The Vineman Ironman, the Vineman Half Ironman, the Hawaiian Half Ironman, and the San Francisco, Avenue of the Giants, and NYC Marathons.

He has worked in finance for over 30 years as a technology investment banker, having worked at Robertson Stephens, Morgan Stanley, Piper Jaffray, Lehman Brothers, Perella Weinberg, and Moelis & Company.

Paul Inouye is the father of two children Miles and Sutton.

Where did the idea for Western Hills Partners come from?

Western Hills Partners is named after the foothills of the mountain range that run along the Peninsula in the Bay Area. My home office looks directly at these beautiful hills overshadowing Silicon Valley and I am often riding or hiking up these hills in my spare time.

The idea for the firm comes from my early roots in banking at Robertson Stephens where I worked with the early entrepreneurs of Silicon Valley. While I have also spent time as a senior banker at bulge bracket firms working with the largest tech players in the Valley, my true professional passion has always been in advising vibrant tech founders and entrepreneurs to build their businesses.

What does your typical day look like and how do you make it productive?

My day is highly varied which is one of the things I love most about my profession. A single day may consist of a 2-hour client call, making outbound marketing calls to buyers or prospective new clients, reviewing an important due diligence-related analytical analysis and work, and collaborating with colleagues on a live project. In addition, I am often researching an industry or a business or creating some new pitch materials for a project on a given day. Each activity requires a unique and distinct skill that really energizes me intellectually.

The key to a productive day for me is to keep a very organized calendar that allocates discrete dedicated time slots to getting each day’s critical agenda items completed. I end each day by reviewing the next day’s agenda and meetings and adjusting my calendar to accommodate any new meetings or important tasks. Then, throughout the day Paul Inouye keep a tracking sheet of items that require follow-up and use that to plan my subsequent workweek. While a bit old-school and rote at times, I have personally found my method to be highly effective and useful.

How do you bring ideas to life?

I am avid about my exercise and use that time to think through business issues and brainstorm ideas whether on long bike rides, runs, or hikes. I take my phone with me at all times and will create brief notes that Paul Inouye will then follow up with at my desk to flesh my thoughts more fully.

As an entrepreneur, I will often also wake up in the middle of the night with a creative thought and have started keeping a journal next to my bed so I can quickly jot down a few key thoughts or ideas that I can follow up within the morning.

What’s one trend that excites you?

Technology, and particularly software, is literally changing the world. What I mean by that is that software is literally disrupting almost every other major industry from payments to supply chains to agriculture to insurance to retail. This is the result of a cadre of highly talented and visionary entrepreneurs rethinking traditional processes and developing new innovative solutions for these industries aimed at improving decision-making via data/analytics or streamlining old inefficient processes.

Paul Inouye have also found WFH and telecommuting to be incredibly productive tools for my workday. Having traveled and commuted extensively throughout my career, I find that the 10-20 hours that I have gotten back to myself have been an exciting new trend. It both helps me be more productive professionally and to be less stressed and fatigued personally. While Covid has been a global pandemic and tragedy, it has had a few silver linings.

What is one habit of yours that makes you more productive as an entrepreneur?

There are actually several habits that have greatly impacted my success as an entrepreneur. One of the most important was the lesson I was taught early on in my career in banking to take ownership of everything I worked on. This ownership mindset is incredibly valuable as Paul Inouye approach my work as if I were the first and last line of defense. Another valuable ethos that I learned in banking was to serve as chief cook and bottlewasher and never believe any job to be beneath myself or above my pay grade to do. Lastly, my deep sense of confidence and resilience have served me well as I am well equipped to take setbacks knowing I have the core skills to overcome nearly every obstacle.

What advice would you give your younger self?

Do more virtual meetings and take fewer flights! Times are they are a-changing! 🙂

In all honesty, I would encourage myself to take more risks and bet on myself more aggressively. Most professionals in banking are risk-averse and prefer to work within the confines of a larger organization but I have found that I truly flourish as my own boss where I can operate with ultimate flexibility.

Tell us something that’s true that almost nobody agrees with you on.

A banker can actually be more effective by taking a less combative stance on issues. I think a pearl of common wisdom is that tech m&a banking is a dog-eat-dog world that requires you to take no prisoners. As I became more senior in banking, I have realized that it was important to develop deep professional relationships with both clients and professionals on the other side of the table as a long career would require dealing with these individuals on multiple occasions as opposed to on series of one-off instances.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I am dedicated to my physical well-being and have maintained a regimented daily exercise routine throughout my career. I am personally at my best post a morning ride or run when I activated my mind and body. I have always done a good job at balancing my professional and personal priorities in a way that complements each other and I don’t believe one can find success in one without finding success in the other.

What is one strategy that has helped you grow your business?

I have found it important to invest wisely in my business. This includes both bringing on additional professionals and core productivity technologies. I recently purchased a very large database of technology businesses. This required sizeable cash payment and literally was an all-in bet on my firm and myself. Similarly, I hired two talented associates to help me scale my business and they have been invaluable in building my practice.

I also believe in creating a work environment that is truly collaborative, respectful, and team-oriented. I have worked at my share of firms that were effectively fiefdoms and sweatshops and where I was miserable. I believe that I can get more out of people who feel that they are truly recognized and valued as core contributors to the team.

What is one failure you had as an entrepreneur, and how did you overcome it?

I was slow to hire a junior team to help grow my business until I realized there would never be enough hours in the day for me to get through each day’s priorities unless I found and hired a team of talented junior resources to assist me. My best decision was to recently bring on two highly talented associates who have helped me materially scale my business.

I also believe in the 80% rule in decision making in which processes are refined as more information and data becomes available versus waiting until one has the perfect information as I have found that only leads to analysis paralysis.

What is one business idea that you’re willing to give away to our readers?

I know that as a small business owner there is nothing more frustrating than when a core part of software or hardware fails as I don’t have the time or expertise to quickly fix these issues. I would gladly pay an organization $200 per employee per month to maintain my IT infrastructure and be on call to put out my IT fires. I have to imagine that my fellow SOHO colleague would similarly find such a service highly valuable.

What is the best $100 you recently spent? What and why?

My annual membership for CLEAR for while I don’t travel as frequently as I used to, I have found it invaluable as it removes so much of the stress of travel is being whisked to the front of the long lines that are back at airports. Rather than glancing at my watch, the TSA line moves along at a glacial pace in front of me, I would much rather grab a healthy meal inside the terminal and casually make my way to my gate than have to sprint to catch my flight.

What is one piece of software or a web service that helps you be productive?

We use Pitchbook for everything from preparing for an upcoming meeting, to looking up trading and deal multiples, to finding buyers for a sell-side assignment, and to researching key new trends and data. I find I use it at least 2-3 daily and it provides great leverage to my team as well.

What is the one book that you recommend our community should read and why?

Never Split the Difference by Chris Voss. Negotiating is an everyday part of our lives and can be difficult and challenging however this book provides insightful and actionable strategies to become a much more effective and successful negotiator. Several of its keen insights are that negotiating requires emotional intelligence, building a connection with the other party, being mindful of the tone of voice you use, not compromising or accepting a counterparty’s deal and taking your time, and being patient to make the best deal.

What is your favorite quote?

“Don’t manage to an outcome. Manage processes.”
“Slow down to hurry up.”
“Bad news isn’t like a fine wine. It doesn’t get better with age.”
“Leaders make the weather.”

Key Learnings:

  • Having a growth mindset – there is so much information available online, once you pick what you want to learn, finding the best educational tools to help you get there is key. But having that intellectual curiosity to continue to learn has paid dividends for both my personal and professional growth.
  • Enjoy the now – It is very easy as an entrepreneur to be thinking 5-10 years out about your strategy, business plans, etc. But if you’re not enjoying it ‘in the now”, is it all worth it? I really enjoy all that I am doing and I love sharing these strategies with other business owners.
  • Do not be afraid to fail. Every great entrepreneur learns from their mistakes and comes back even better having learned from the pain.
  • Find a mentor to gain a new perspective.
  • Learn that neither rejection nor failure is the end of the world.
  • Use data to help you set goals and expectations.
  • Read “What You Do Is Who You Are: How To Create Your Business Culture” by Ben Horowitz.
  • Do things right the first time, even if it might take a long time.