aug. 1, 2025

MyEO Wine Tour & Karaoke Bus

EO Members & Plus-Ones
Friday, August 1, 2025, 9:30a - 6:00p
Meetup location TBA

Wine Tastings, Karaoke, and EO Friends!

Join us for an unforgettable day of wine tasting and karaoke fun with fellow EOers! We’ll tour some of the best spots in the Willamette Valley, sip on delicious wines, enjoy a scenic lunch, and belt out our favorite tunes on the Solid Gold karaoke bus.

$149 per person. Don’t forget your singing voice! Spots are limited.

aug. 12, 2025

EO Happy Hour: Keys Lounge

EO Members & Strategic Alliance Partners
Tuesday, August 12, 2025, 4:00p - 7:00p
Keys Lounge
533 NE Killingsworth St.

Classic Midcentury Cocktails Inside a 1962 Locksmith Shop

Join this happy hour with peers in the EO community, at the lauded Keys Lounge in NE Portland. A fun opportunity to connect with fellow entrepreneurs and enjoy the summertime together.

We'll pick up the tab for drinks, food is on you! We hope this will be a fun and casual time to relax and connect with fellow entrepreneurs.

aug. 22, 2025

The Solve Session: A Root-Cause Workshop

EO Members Only
Friday, August 22, 12:00p-2:00p
Location TBA

Get to the root cause of your challenge.

In this intimate, hands-on workshop limited to just 7 participants, EOS Implementer Eliot Wajskol will guide you through a focused process to uncover the root cause of a real business challenge you’re facing and define a set of clear, actionable steps to break through and move forward.

Using a proven approach rooted in the IDS™ (Identify, Discuss, Solve) framework, you’ll go beyond surface-level symptoms. You'll work through a tailored, deep-dive experience designed to spark meaningful momentum in your business.

This isn't a lecture. This is a working session. You’ll bring a real challenge. You’ll leave with real traction.

Sept. 4, 2025

Tenured Member Dinner + Alternative Investments Panel

Tenured EO Members Only
Thursday, September 4, 2025, 5:00p - 8:00p
Andina
1314 NW Glisan St.

Private market and alternative investments for entrepreneurs: How successful entrepreneurs can reduce the risk of concentrating wealth in their own companies while still achieving attractive long-term returns.

Many entrepreneurs would like to diversify their resources outside of their business, but are reluctant to trade the returns they achieve internally with those historically experienced in public stock and bond markets. In this informative, interactive workshop we will explore how investment into private markets and alternatives can potentially provide ROAs greater than public markets while reducing concentration risk.

Presented by SKA Wealth Strategies of Raymond James, our speakers will include Iris Lee and Carlos Munoz-Lucas of Raymond James Alternative Investments Group, Angelo Gutierez, Private Credit specialist with Blue Owl, and Aron Healey, Alternative Investments specialist with Neuberger Berman.

Due to regulatory investor qualification requirements, this presentation will be most suitable for individuals with investible assets of at least $2.2 million.

Dinner is included.

Sept. 12, 2025

New Tax Law, Big Tax Savings: What Owners & Investors Need to Know Now

EO Members & Strategic Alliance Partners
Friday, September 12, 12p-2p
Pacific West Bank - 3rd Floor Hawthorne Room
1300 SW 5th Ave. #300

The tax landscape for business owners just changed—dramatically. On July 3, 2025, Congress passed the sweeping One Big Beautiful Bill Act, unlocking powerful new tax savings opportunities for entrepreneurs, real estate investors, and growing companies.

Join us for a high-impact seminar on Friday, September 12 at 12:00pm, where we’ll break down what’s in the bill and how to take immediate action to lower your taxes.

Topics will include:

• How to fully deduct R&D expenses again—retroactively

• Maximize 100% bonus depreciation to build wealth fast

• Making the most of the now-permanent 20% pass-through (QBI) deduction

• Tax-free gains with Qualified Small Business Stock (QSBS)

• Hidden savings most business owners will miss without strategic planning

Whether you’re running a service-based business, scaling a manufacturing company, or investing in real estate, this session will equip you with the insights you need to capitalize on the biggest tax overhaul since 2017.

Lunch is included.

Sept. 19, 2025

Hopscotch Social with EO Las Vegas

EO Members Only
Friday, September 19, 2025, 5:00p - 7:00p
Hopscotch
1020 SE 10th Ave.

Portland meets Vegas! While EO Las Vegas is in town for their chapter retreat, we’re teaming up for a night of social connection at Hopscotch—Portland’s trippiest interactive art experience that blends immersive light, sound, and tech installations into something unforgettable. If you’ve never been, it’s like stepping into a dreamscape you can walk through.

We’re covering your entry ticket and your first drink—just show up ready to connect with fellow entrepreneurs in a setting that’s anything but ordinary.

Feeling social? Stick around after for dinner at Wonderlove, the new food cart pod from EO Portland alum Joel Beaudoin (you’ll buy your own bites, but the company will be excellent).

Registration closes September 12. No walk-ins.

Sept. 24-25, 2025

Catalyst Summit: Analog/Us

This event is public, designed for business owner-operators only. The first 70 EO Members to register get free registration! Use code “eo2025” to access free ticket.

Kickoff — Wednesday, Sept. 24, 4:00p-7:00p at Show Bar
Full Day Event — Thursday, Sept. 25, 9:00a-5:00p at Irving St. Studio (Ecotrust)

Join the Summit

The fifth annual Catalyst Summit, powered by Kinesis and the Entrepreneurs' Organization of Portland, is created by and for the owner-operated business community. With no sponsors or sales pitches, Catalyst offers a space where peers openly share insights through talks, panels, workshops, and imaginative breakouts. Every detail, from the agenda to the setting, is designed to foster real conversations, bold ideas, and lasting impact. Attendees won’t just listen; they’ll engage, explore, and generate ideas they’ll still be thinking about years later.

Our 2025 Theme: Analog/Us

In a world of pings, posts, and push notifications, we’re all craving real presence. Our fifth Catalyst Summit invites us to disconnect and reconnect — to slow down and tune in to a more meaningful shared experience.

Why Analog/us? While digital signals are binary 0s and 1s, analog is the frequency of us: continuous, multi-dimensional, tactile. Leaders are starting to attune to that frequency: one that values creation and intention over endless activity. This year, we’re dialing down the noise and turning up the signal — the conversations that spark when we’re in the room, the ideas that emerge between the lines, the “us” that only happens offscreen.

Together, we'll explore:

• New ways of connecting — with clients, customers, employees, and beyond — that integrate or rediscover the in-person, touchable, and tangible

• How visionary leaders are creating meaningful spaces and experiences that connect with their audience and/or community

• What helps a community cohere in an age of disconnection and fragmentation

Oct. 7, 2025

Relationable: Tools for Thriving in Your Most Meaningful Relationships

EO Members Only
Tuesday, October 7, 2025, 4:00p-7:00p
Bar West
1221 NW 21st Ave.

Tools for Trust, Honesty, and Clear Expectations in Your Life's Most Meaningful Relationships

Join this MyEO event developed by Justin M. Riordan, EO Portland Alumni, author of The Monogamy Spectrum, and founder of the RELATIONABLE framework—a tested and powerful communication system born out of the real-world lessons of a 25-year-long cutting edge marriage.

When Justin and his husband set out to build a lasting relationship, there was no roadmap, so they had to create their own. What started as a personal survival tool evolved into a repeatable strategy for managing high-stakes relationships of all kinds—romantic, business, and everything in between.

This isn't about scandal or drama—it's about clarity, commitment, and conscious connection. With cocktails.

RELATIONABLE is designed for entrepreneurs who want to lead more effectively at home and at work. Whether you're navigating a business partnership, managing a team, deepening personal connections, or trying to defuse conflict before it derails your vision, this framework delivers.

In this eye-opening conversation, we’ll explore:

• How to set relationship rules without assuming you're on the same page

• Why a simple reporting system can transform trust and reduce drama

• What it looks like to reward honesty—even when it’s hard to hear

The ticket fee covers all your happy hour drinks & appetizers. The speaker's time is donated.

Oct. 21, 2025

EO Tales of the Living Dead

EO Members Only
Tuesday, October 21, 2025, 7:00p - 10:30p
Raven’s Manor
235 SW 1st Ave.

An evening of raw truth, resilience, and redemption — let's get vulnerable and hear incredible stories.

Behind every triumph lies a story untold — the setbacks, failures, and near-business-death experiences that shaped the peers we admire today. We read the headlines, but we rarely hear the full, unfiltered journey... the dark parts and heartache we rarely speak of.

In this intimate gathering, EO members are invited (but never pressured) to take the open mic to share a story they usually don’t — the dark nights of the soul, the gut-wrenching failures, the moments when everything was on the line. No polish, no pretense — just honest reflections for the benefit of our community.

Expect laughter, goosebumps, maybe even a tear or two. Most of all, expect to leave feeling deeply connected and inspired by the resilience of your fellow entrepreneurs.

We'll also enjoy food and drink at the spooky-themed Raven's Manor!

Oct. 29, 2025

The Legal Landscape: Regulatory Shifts from DC to Oregon

EO Members, SAPs, Key Execs
Wednesday, Oct. 29, 2025, 12:00p - 2:00p
Location TBA In-Person

Did you know that Oregon State had a record number of new bills introduced this session?

This means lots of changes you need to know about. Staying ahead of legal updates isn’t just smart, it’s essential—yet nearly impossible! Join our SAP Equinox Business Law Group's founder and EO Seattle member, Michelle Bomberger, to unpack key legal and regulatory developments from the past year at both the federal level and in Oregon State law.

Tailored for entrepreneurs and business owners who prioritize strategic growth and proactive risk management, this session will highlight changes that impact your operations, contracts, hiring practices, and compliance obligations, giving you the clarity and foresight you need to make confident decisions as you plan for 2026 and beyond.

What you'll learn:

• Major regulatory and legal updates from 2024 and early 2025

• How federal changes intersect with Oregon-specific rules

• Practical strategies to mitigate risk and stay compliant

• Legal trends to monitor

Lunch is included.

Nov. 6, 2025

EO Dine Around the Table

EO Members and Spouses/Life Partners
Thursday, November 6, 2025, 6:00p-9:00p
Multiple homes around Portland

A Surprise Dinner Party with Time Built In for 5% Conversation

EO Members and Spouses/Life Partners are invited to sign up for an intimate dinner at an EO Member's home in the Portland area on Thursday, November 6.

Each home will feature meal lovingly prepared by an EO Member. Dietary restrictions will be taken into account, but meals will be a surprise.

This fall, every dinner party will feature a directed 5% conversation on Legacy: It's Not How You Find the World, But How You Leave It.

Get ready for meaningful connections with other EO Members!

What to Bring:

1. A bottle of your favorite wine to share

2. Your vulnerability! Get ready for a deep conversation over great food.

While the menus are unique, every location will feature:

1.⁠ ⁠Cocktail Hour + a Get-to-Know-You Opener

2.⁠ ⁠Dinner + Deep Dive Topical Discussion

3.⁠ ⁠Dessert + Social Time

Nov. 13, 2025

From Commodity to Category of One — With Brittany Hodak

EO Members and SAPs
Thursday, November 13, 2025, 3:00p-7:00p
Location TBA

How to Immediately Boost Your Reputation, Referrals, and Revenue

Why should a customer choose your agency, team, or carrier over any other option? If you can’t answer that clearly and confidently, they’ll go with someone who can.

In this dynamic keynote, you’ll learn how to build trust, humanize your sales process, and create loyalty that lasts beyond price comparisons — turning customers/clients into superfans who renew, refer, and advocate for your brand.

Key takeaways:

• Why the most effective sales tool in human history has worked for millennia

• How to make commodity factors like pricing and timing much less relevant to customers

• What to change today to immediately improve sales performance

Dec. 18, 2025

The EO Holiday Party

EO Members, Strategic Alliance Partners, Accelerators, and Significant Others
Thursday, December 18, 2025, 7:00p - 11:00p
Castaway Portland
1900 NW 18th Ave.

It's the party of the season!

The lights are twinkling, the mood is just right,
Good friends, good cheer, and laughter all night.
Grab something sparkly, bring your best cheer—
It’s the holiday bash of the year!

Cocktail attire encouraged. More details coming this fall!