In Search Of Excellence

Fifty meetings with venture capital firms. Not a single yes.

Before Jamie Siminoff founded Ring, that was his reality while trying to fund an earlier company. Then a New York Times story helped him raise $5.7 million—and he discovered why having too much money can create problems of its own.

In Part One of my conversation with Jamie, we get into questions founders ask me every day: How do you get in front of investors? Do you need a co-founder? Is a PR firm worth the money? And how much capital should you actually raise?

Jamie takes me back to cleaning horse stalls before school, selling electronics door to door at Babson, and teaching himself to run a telephone network after his business partner left. We also talk candidly about being bullied, how those experiences shaped both of us, and why success doesn't erase them.

His story about paying back creditors gets to something I care deeply about: how you treat people when the business is struggling. He explains how being honest with them helped him work out a way forward, rebuild, and pay them back. These are the decisions I want aspiring entrepreneurs to hear about alongside the successes.

CHAPTERS
00:00 Highlights and introduction
01:38 Family influence and Jamie's earliest inventions
06:26 First jobs: pulling weeds and driving forklifts
11:10 What cleaning horse stalls taught Jamie
15:34 Bullying and its lasting impact
22:50 Finding mentors and learning from successful people
26:00 The Land Rover deal that changed Jamie's motivation
29:02 Childhood experiments and dangerous mistakes
32:08 Teachers, craftsmanship, and taking pride in your work
36:45 The conversation that led Jamie to Babson
39:15 Starting businesses on campus
43:39 Turning business plans into a business
49:00 Learning the telecom business from scratch
56:01 Paying creditors when things go wrong
58:04 Do you need a co-founder?
1:00:18 Fifty VC meetings without a yes
1:02:17 How to earn a meeting with investors
1:05:20 The New York Times breakthrough
1:06:24 Should a startup hire a PR firm?
1:08:06 Choosing investors—and the danger of raising too much
1:12:25 Part Two preview

If you want to prepare more effectively for investor meetings, DM me the word COACHING on Instagram.

ABOUT RANDALL KAPLAN
Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder of JUMP Investors, and host of In Search of Excellence. His Extreme Preparation methodology emphasizes thoughtful preparation, discipline, and execution in business and life.

WORK ONE ON ONE WITH RANDALL
Coaching: https://www.randallkaplan.com/coaching

WATCH MY TEDx TALK
How to Get Your Dream Job with Extreme Preparation | Randall Kaplan | TEDxTampa
https://www.youtube.com/watch?v=MIvlFpoLfgs

LISTEN TO IN SEARCH OF EXCELLENCE
YouTube: https://www.youtube.com/@randallkaplan
Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L
Podcast website: https://www.insearchofexcellence.com/

FOLLOW RANDALL KAPLAN
Instagram: https://www.instagram.com/randallkaplan/
LinkedIn: https://www.linkedin.com/in/randallkaplan/
TikTok: https://www.tiktok.com/@randall_kaplan
X: https://x.com/RandallKaplan
Website: https://www.randallkaplan.com/

#InSearchOfExcellence #RandallKaplan #JamieSiminoff #Entrepreneurship
About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.

Coaching and Staying Connected:
1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

You can spend seven days changing your life—and return home to discover that your old patterns are still waiting for you. So how do you make personal growth last?

In Part 2 of my conversation with Matt Brannagan of the Hoffman Institute, we get into what happens AFTER the Hoffman Process: the difficult conversations, the return to everyday life, and the ongoing work of becoming the person you want to be.

I share what it was like to tell my parents “I forgive you and I love you,” why I made a major mistake by going straight home after the retreat, and how quickly familiar circumstances brought back behaviors I thought I had changed.

Matt explains why lasting growth isn’t about never getting triggered again. It’s about noticing your patterns sooner, reducing how intensely and how long they control you, and choosing a better response.

We also discuss vulnerability, the extraordinary connections formed in a group of strangers, the difference between the Hoffman Process and therapy, why preparation matters, and what seven days without a phone can teach you about yourself.

One of my biggest takeaways is simple: awareness alone isn’t change. You need reminders, support, and the willingness to keep doing the work long after the retreat ends.

The goal isn’t perfection. It’s becoming calmer, more present, more thoughtful, and more intentional—one decision at a time.

CHAPTERS

00:00 Forgiving your parents—and starting a difficult conversation
03:49 What happens when the seven-day retreat ends?
07:08 My biggest mistake after the Hoffman Process
08:17 Does the transformation fade over time?
09:47 Measuring progress: shorter, less intense patterns
12:44 The ten patterns I keep on my desk
13:50 Hoffman teachers versus traditional therapists
16:32 How vulnerability changed our group
19:04 Can Hoffman and therapy work together?
20:25 Why preparation creates safety
22:15 Inside the retreat: rooms, food and long days
25:58 Seven days without a phone or distractions
27:34 Why boundaries matter during the retreat
29:49 The person I want to become
30:51 What Matt wants prospective participants to know
34:05 Would I do the Hoffman Process again?
35:18 Cost, scholarships and accessibility
37:12 Final reflections

ABOUT MATT BRANNAGAN

Matt Brannagan is CEO of the Hoffman Institute Foundation and Chair of Hoffman Institute International. A U.S. Army veteran and former Master Resilience Trainer, he joined Hoffman in 2007 and has served as a teacher, coach, Director of Faculty, and Chief Operating Officer.

Learn more: https://www.hoffmaninstitute.org/

ABOUT RANDALL KAPLAN

I'm a serial entrepreneur, venture capitalist, co-founder of Akamai Technologies, early investor in Google, and host of In Search of Excellence.

Through my Extreme Preparation® methodology, I coach founders, CEOs, executives, business owners, and ambitious professionals to achieve extraordinary personal and professional results.

PRIVATE COACHING — WORK WITH ME

I privately coach a limited number of high achievers who want to elevate their careers, scale their businesses, overcome obstacles, and reach higher levels of success personally and professionally.

If you're ready to invest in yourself and make meaningful changes in your life, I'd love to hear from you.

Learn more or inquire about coaching:
https://www.randallkaplan.com/

Or DM me COACHING on Instagram: @randallkaplan

WATCH, LISTEN & SUBSCRIBE

YouTube: https://www.youtube.com/@randallkaplan

Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310

Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L

Podcast website: https://www.insearchofexcellence.com/

CONNECT WITH RANDALL

Instagram: https://www.instagram.com/randallkaplan/

LinkedIn: @randallkaplan

TikTok: @randall_kaplan

X: https://x.com/RandallKaplan

Personal website: https://www.randallkaplan.com/

WATCH MY TED TALK

How to Get Your Dream Job with Extreme Preparation

https://www.youtube.com/watch?v=MIvlFpoLfgs

JOIN THE CONVERSATION

What is one pattern you recognize in yourself that you would like to change?

Share your thoughts in the comments. If you found this conversation valuable, please like the video, subscribe to In Search of Excellence, and share this episode with someone who might benefit from it.

#HoffmanProcess #PersonalGrowth #EmotionalIntelligence #SelfAwareness #Forgiveness #InSearchOfExcellence #RandallKaplan
About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.

Coaching and Staying Connected:
1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

What happens when you achieve the success you dreamed of and still don’t feel okay?

I went to the Hoffman Institute during a painful divorce, and I was terrified of confronting things I had buried for years. It’s something that most of us don’t think about until it’s too late:  mental health deserves the same attention we give our physical health. In this emotional and bare-it-all conversation, I share what it took to face some of my own patterns and face the demons of my childhood that have been holding me back my entire life and influencing the way I’ve lived for my entire life..

In Part 1 of In Search of Excellence, I sit down with Hoffman Institute CEO Matt Brannagan to talk about the Hoffman Process: a week-long personal-growth retreat that helps people examine patterns learned in childhood. According to the Hoffman Institute, the Process has helped more than 150,000 people since 1967.

I share what frightened me about attending, what Scooter Braun told me beforehand that prevented me from backing out at the last minute, and why the 10-page questionnaire brought me to tears many times. We discuss a friend who earns $50 million a year but hated going to work, and why achievement doesn’t always bring fulfillment.

Matt explains how Hoffman influenced his leadership during his deployment in Iraq, Bob Hoffman’s “negative love syndrome” framework, and the Quadrinity: emotions, intellect, body, and spirit. We also discuss forgiveness, parenting, and why recognizing a pattern is only the beginning of changing it.

In this conversation
• Why success and money can leave happiness unresolved.
• How childhood patterns can affect your relationships and work.
• Why self-awareness alone may not change your behavior.
• How understanding your parents can open the door to forgiveness.

Chapters
00:00 - Success and the search for happiness
00:54 - From Hoffman to Iraq
03:52 - From Hoffman student to CEO
06:34 - How Bob Hoffman created the Process
09:58 - You achieved your goals but still feel empty
16:03 - What Scooter Braun told me before Hoffman
25:49 - How childhood shapes the way we seek love
31:40 - Your personality or a pattern you can change
36:20 - The Quadrinity explained
44:41 - Making $50 million and hating your job
48:06 - How emotional stress shows up in your body
52:07 - What Hoffman means by your spiritual self
54:14 - The work that starts before you arrive
56:32 - The questionnaire that brought me to tears
1:06:56 - Why self-awareness alone is not enough
1:09:58 - The letter that helped me forgive my parents

About Matt Brannagan
Matt Brannagan is CEO of the Hoffman Institute Foundation and Chair of Hoffman Institute International. A U.S. Army veteran and former Master Resilience Trainer, he joined Hoffman in 2007 and has served as a teacher, coach, Director of Faculty, and Chief Operating Officer. He holds a master’s degree in transpersonal psychology and is a doctoral candidate in clinical psychology.

Hoffman Institute: https://www.hoffmaninstitute.org/

About Randall Kaplan
Randall Kaplan is a serial entrepreneur, venture capitalist, co-founder of Akamai Technologies, early Google investor, and host of In Search of Excellence. Through his Extreme Preparation® methodology, he coaches founders, executives, business owners, and ambitious professionals on achieving their personal and professional goals.

Join the conversation
Which pattern would you most like to change: overworking, perfectionism, or avoiding difficult conversations? Tell us in the comments. Like the video, subscribe to In Search of Excellence, and turn on notifications for Part 2. Share this with someone who needs to hear that asking for help is a strength.

Want to work one on one with me
I privately coach a limited number of high achievers who want to elevate their careers, scale their businesses, and reach higher levels of success professionally and personally. To apply to work with me, visit https://www.randallkaplan.com/

Listen and connect
Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L
All episodes: https://www.insearchofexcellence.com/
Extreme Preparation TEDx Talk: https://www.youtube.com/watch?v=MIvlFpoLfgs

Follow Randall
Instagram: @randallkaplan
LinkedIn: @randallkaplan
TikTok: @randall_kaplan
X: https://x.com/RandallKaplan

Support
If you’re struggling or in crisis in the U.S., call or text 988 for free, confidential support, 24/7. Online chat: https://988lifeline.org/

#HoffmanProcess #MentalHealth #InSearchOfExcellence
About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.

Coaching and Staying Connected:
1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

What if an affair isn't where a marriage first breaks, but the moment years of disconnection finally become impossible to ignore?

After more than 25 years and 1,000 matrimonial cases, renowned divorce lawyer Jim Sexton reveals the five types of infidelity, the warning signs couples routinely miss and the painful question betrayed partners almost never ask.

In Part 3 of this extraordinary conversation with Randall Kaplan, Jim begins with one of the most shocking prenuptial agreements he has ever encountered: a clause that reduced a wife's alimony by $50,000 for every ten pounds she gained. The judge called the provision disgusting, but upheld it.

Jim then explains how marriages can slowly unravel when couples stop doing the seemingly insignificant things that once made their partners feel noticed, desired and loved. Neither person may recognize the damage while it is happening. By the time an affair occurs, it may be the final symptom of a relationship that has been deteriorating for years.

Randall and Jim explore:
• The five distinct types of infidelity
• When flirting crosses the line into cheating
• Why revenge affairs create more pain instead of relief
• Whether sex addiction can become an excuse for avoiding deeper problems
• The questions men and women commonly ask after discovering an affair
• Why learning every sexual detail may make healing more difficult
• The conversation couples should have before resentment becomes betrayal
• Whether trust and intimacy can be rebuilt after infidelity
• Why opening a struggling marriage is often treated as a final Hail Mary
• When divorced parents should introduce a new partner to their children
• How to protect children from loyalty conflicts after divorce
• Why preparation and organization have been essential to Jim's success

Jim also opens up about his own dating life, the freedom and responsibilities of being single, his relationship with his sons and the grief of knowing that the people and animals we love will not be with us forever.

The conversation closes with Jim's deeply personal reflections on love, success and mortality, including the one message he would leave his sons if he had only 60 seconds to live.

Jim also tells Randall that this was one of the most comprehensive interviews he has ever done and calls Randall's Extreme Preparation "shocking to be on the other side of."
What causes more damage to a marriage: the act of cheating or the years of disconnection that often precede it?

Share your answer in the comments. If this conversation made you reconsider love, loyalty or marriage, please like the video, subscribe to In Search of Excellence and share this episode with someone who needs to hear it.

Timestamps
00:00  Getting caught cheating versus confessing
00:28  Who should never get married?
01:55  The disgusting prenup clause a judge upheld
07:03  How small acts of neglect can predict a divorce
11:44  When does flirting become cheating?
16:43  Jim Sexton's five types of infidelity
25:10  Is sex addiction real or sometimes an excuse?
27:14  Can someone cheat and still have a happy marriage?
33:50  What betrayed partners ask after an affair
39:04  The painful question almost nobody asks
43:10  Do open marriages work?
47:43  Why preparation is the foundation of Jim's success
51:20  When should children meet a new partner?
57:31  Protecting children during and after divorce
1:03:21  Accepting what you cannot control
1:11:11  Jim's honest answer about his dating life
1:17:04  Jim plays Fill in the Blank to Excellence
1:21:43  Jim's final message to his sons
1:22:11  Why Jim called this one of his most comprehensive interviews

About Jim Sexton
James J. Sexton is a leading matrimonial and family law attorney who has handled more than 1,000 cases during over 25 years in practice. He is the bestselling author of If You're in My Office, It's Already Too Late and How to Stay in Love. His candid insights into marriage, divorce, infidelity and relationships have made him one of the world's most widely watched legal voices.

Connect with Jim Sexton
Website: https://www.nycdivorces.com/
Instagram: https://www.instagram.com/nycdivorcelawyer
YouTube: https://www.youtube.com/@sextonshow
TikTok: https://www.tiktok.com/@nycdivorce

Watch Parts 1 and 2
Part 1: https://www.youtube.com/watch?v=_qKNSync_uw
Part 2: https://www.youtube.com/watch?v=NrHjXLgBUVo

Listen to In Search of Excellence
Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310
Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L
All episodes: https://www.insearchofexcellence.com/

Work One on One with Randall Kaplan
Randall privately coaches a limited number of entrepreneurs, executives and high achievers who want to accelerate their personal and professional success.

Apply here: https://www.randallkaplan.com/

Extreme Preparation TEDx Talk: https://www.youtube.com/watch?v=MIvlFpoLfgs
About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.

Coaching and Staying Connected:
1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X

Divorce lawyer Jim Sexton has spent nearly 30 years watching marriages fall apart - and he knows the mistakes couples make long before they ever enter a courtroom.

In Part 2 of my conversation with Jim Sexton, one of the country’s most experienced divorce attorneys, we go deep on marriage, divorce, prenups, monogamy, sexual compatibility, dating, choosing the right partner, divorce statistics, and what actually makes relationships last.

Jim has represented executives, entrepreneurs, CEOs, athletes, celebrities, and high-net-worth families through some of the most difficult divorces imaginable. After decades on the front lines of family law - and after going through divorce himself - he has developed some fascinating and sometimes controversial views about love, marriage, sex, money, and relationships.

We talk about why getting married may be one of the most legally significant decisions you’ll ever make, despite most people having almost no idea what they are legally agreeing to.

Jim explains why the best divorce lawyer may actually be the lawyer who keeps you out of court, why spending $10,000 fighting over $5,000 makes no sense, and why divorce should eventually be approached more like a business transaction than an emotional battle.

We discuss whether prenups are unromantic, whether they actually hold up in court, and why Jim argues that a thoughtfully constructed prenup can actually create greater emotional and financial safety in a marriage.

Then we get into some of the most controversial research and observations surrounding sexual history, sexual satisfaction, monogamy, marriage success, and divorce.

It’s a conversation about how to choose the right person, build a stronger relationship, understand what marriage actually means, and avoid mistakes that can cost you emotionally and financially for years.

TIMESTAMPS

00:00 — The legal reality of marriage almost nobody understands
05:45 — Why a great divorce lawyer may actually keep you OUT of court
12:53 — How to find a great divorce attorney without trusting Google rankings
18:44 — The “Sopranos strategy” before divorce—and why Jim says it can backfire
24:27 — Why Jim Sexton says every first date is basically a sales call
29:59 — The fear that stops people from making the move they actually want
34:20 — The 3 real reasons people get married
41:30 — Who probably should NOT get married
46:07 — “Everyone has a prenup” — Jim explains what most couples don't realize
51:41 — How long should you date before getting married?
59:38 — Do more sexual partners increase the likelihood of divorce?
1:07:42 — Jim's controversial definition of successful monogamy
1:20:11 — Why divorce rates rise dramatically after the first marriage
1:31:12 — Do prenups actually work? What they can—and cannot—protect

ABOUT JIM SEXTON

Jim Sexton is a veteran matrimonial and divorce attorney with nearly three decades of experience handling complicated divorce, custody, financial, and family-law disputes.

Throughout his career, Jim has represented high-net-worth individuals, entrepreneurs, CEOs, executives, athletes, and celebrities while developing a reputation as an experienced courtroom strategist and negotiator.

ABOUT RANDALL KAPLAN

Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of the In Search of Excellence podcast.

Through his Extreme Preparation™ methodology, Randall helps founders, executives, business owners, entrepreneurs, and ambitious professionals improve their strategy, communication, preparation, decision-making, and execution so they can achieve extraordinary results in business and life.

WHAT DO YOU THINK?

Should everyone get a prenup before getting married?
How long should couples date before marriage?
And what matters most to a successful long-term relationship: love, compatibility, communication, sexual chemistry, financial compatibility—or something else entirely?

WANT TO WORK ONE-ON-ONE WITH ME?

I privately coach a limited number of founders, executives, business owners, entrepreneurs, and other high achievers who want to elevate their careers, scale their businesses, make better decisions, and reach higher levels of success professionally and personally.

If you're ready to change your life and achieve your goals, apply here:
www.randallkaplan.com

WATCH MY EXTREME PREPARATION™ TEDx TALK
How to Get Your Dream Job with Extreme Preparation
https://www.youtube.com/watch?v=MIvlFpoLfgs

LISTEN TO IN SEARCH OF EXCELLENCE

Apple Podcasts:
https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310

Spotify:
https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6L

For more information:
www.randallkaplan.com
FOLLOW RANDALL

Instagram: @randallkaplan
LinkedIn: @randallkaplan
TikTok: @randall_kaplan
X / Twitter: https://x.com/RandallKaplan
Website: www.randallkaplan.com
1-on-1 Coaching: www.randallkaplan.com
About Randall Kaplan: Randall Kaplan is a serial entrepreneur, venture capitalist, executive coach, co-founder of Akamai Technologies, founder and CEO of JUMP Investors, and host of In Search of Excellence. Through his Extreme Preparation™ methodology, he helps founders, executives, business owners, and ambitious professionals improve strategy, communication, decision-making, and execution.

Coaching and Staying Connected:
1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn | X