"Every meeting gives us another competitive advantage."
Jim Bunch
Founder & CEO
PORTLAND SPEAKEASY CHAPTER
The Right Room
Changes Everything
A private, curated monthly in-person mastermind for established entrepreneurs who want better decisions, stronger relationships, and access to the people, partnerships, and opportunities that accelerate growth.
Come experience Speakeasy at an upcoming Portland meeting.
Your first event is complimentary. Attendance is subject to qualification.
Who You’re Around Determines How Far You’ll Go
Every member is vetted to bring real expertise, valuable connections, and a genuine desire to help others win.
27+
Live and Launching Chapters
592+
Curated
Entrepreneurs
$1.3B+
Annual Revenue
Represented
35k+
Business
Connections
No Entrepreneur Wins Alone.
At a certain level, the hardest part of business isn't finding more information. It's finding the right people to talk to.
Because the bigger the company gets, the fewer people you can really talk to about it. It’s lonely - it's painful.
And you need…
People who've faced the decisions you're facing. People who will tell you what they really think. People who can say
“I've been there. Here's what I'd do.”
Your first event is complimentary. Attendance is subject to qualification.
Your Personal Board of Advisors.
Imagine having a room of accomplished entrepreneurs you actually trust
Better Decisions
Get candid feedback from entrepreneurs who've already faced what you're facing.
Real Solutions
Bring the problem. Leave with strategies, resources, and people who can help solve it.
POWERFUL INTRODUCTIONS
Access partners, talent, customers, vendors, investors, and opportunities you may never find on your own.
AHEAD OF THE CURVE
See what entrepreneurs are actually doing right now in AI, marketing, sales, technology, and growth.
LIFE LONG FRIENDSHIPS
Build friendships whith people who understand this part of your life because they're living it too.
What Happens When
You Get in the Right Room
See What Speakeasy Is Like for Yourself
You’ve heard from our members. Now experience the room firsthand. If you’re a qualified entrepreneur, we’d love to invite you to an upcoming Portland event to meet the members, join the conversation, and see if Speakeasy feels like the right fit for you (and vice-versa).
No Speakers. No Pitches.
No Awkward Networking.
Once a month, your Portland chapter gets together for three hours.
Dinner. Drinks. Real conversation.
Members talk openly about what's working, what's not, the decisions they're wrestling with, and the opportunities they're pursuing.
Then the room gets involved.
Ideas are challenged.
Playbooks are shared.
Introductions are made.
Problems get solved.
Real business gets done here.
Local Relationships. Global Access.
Your Portland chapter becomes your trusted inner circle.
But your membership reaches far beyond one room.
Your Monthly Mastermind
Meet monthly with 15-30 established entrepreneurs in your city, to solve real challenges, share what’s working, uncover opportunities, and make better decisions faster.
A Global Community App
Our community app connects you with hundreds of Speakeasy members to ask questions, share wins, find resources, collaborate, and build valuable relationships.
Visit Other Chapters
Your membership travels with you. Visit Speakeasy chapters in other cities, join their meetings, and walk into a trusted community wherever business or travel takes you.
The Online "Insider Sessions"
Exclusive online training sessions led by experts from within the Speakeasy community - sharing the strategies, tools, and ideas working right now in AI, marketing, leadership, sales, branding, growth, and more.
Notes From Every Chapter
The best ideas from every monthly meeting are captured and available to you via our AI engine - giving you access to the strongest strategies, resources, insights, and breakthroughs emerging from every room.
Online Speed Networking Services
Meet More Members, Faster. Join fast-paced virtual networking events designed to spark new relationships, collaborations, introductions, referrals, and opportunities across the entire Speakeasy network.
Find the Right Person Inside Speakeasy
Quickly discover who’s inside, what they know, and how they can help, while making your own expertise visible to the community.
Your AI Powered Knowledge Hub
Search the collective intelligence of Speakeasy to uncover relevant strategies, resources, conversations, and the members best equipped to help you move forward.
The Annual Speakeasy Experience
Search the collective intelligence of Speakeasy to uncover relevant strategies, resources, conversations, and the members best equipped to help you move forward.
Meet Your
Portland City Chapter Captain
David Baer
Direct Response Marketer • Revenue Growth Strategist • Portland Chapter Captain
David Baer is a veteran direct response marketer with nearly 30 years of experience helping businesses grow through smarter marketing. He began his career in email marketing in 1996 and has since worked across wine, Facebook advertising, online education, workshops, and consulting. Since 2017, he and his partner Ken Cook have led The Prepared Group, advising 7- and 8-figure businesses in industries including manufacturing, industrial, and construction.
Meet Your
Portland City Chapter Co-Captain
Ken Cook
Revenue Strategist • Growth Systems Expert • Portland City Chapter Co-Captain
Ken Cook is a revenue strategist and co-founder of The Prepared Group, where he helps B2B companies build more predictable, scalable growth systems. With more than 20 years of experience, he specializes in connecting marketing, sales, and operations so business leaders can see what is actually driving revenue. He is also the creator of The Predictable Revenue Framework, built to replace disconnected tactics with a more integrated approach to growth.
As Portland’s Co-Captain, Ken brings a clear, systems-focused perspective to the room—helping entrepreneurs identify gaps, improve alignment, and make better decisions around growth. Members gain stronger visibility into what is working, clearer priorities, and a more predictable path to revenue.
Is This Your Kind of Room?
Speakeasy is intentionally curated.
You'll probably feel at home here if...
You've built something real
Speakeasy is for established entrepreneurs who want to grow to the next level. Most members qualify through one of three paths: they lead a business generating at least $1,000,000 in annual gross revenue; they are solopreneurs earning at least $200,000 in annual personal income; or they have recently built and exited a significant company.
These are guideposts, not the only factors. We also consider each person’s experience, accomplishments, growth trajectory, mindset, and potential contribution to the group.
You're still hungry.
You're successful - but you're nowhere near finished. And you’re still in the trenches.
You want relationships, not transactions.
You're looking for trusted peers and not prospects to pitch.
You want honest feedback.
You'd rather hear the truth than have people agree with you.
You show up.
The real value comes from building relationships month after month.
The Best Way to Understand Speakeasy
Is to Experience It.
Don't decide whether you want to join. Just come see what happens when you get in the right room.
Meet David. Meet the members. Share a meal. And join the conversation. Then decide whether Speakeasy feels like the kind of room you've been missing.
Your first Portland meeting is complimentary.
* Attendance is subject to qualification.
A Few Questions
How much does membership cost?
Membership is $5,995 per year. But you don't need to make a membership decision before experiencing Speakeasy.
Who qualifies?
Most members own businesses generating $1M+ annually, or earn $200K+ per year as an owner, or recently exited a company. We also consider experience, trajectory, accomplishments, and what you'll bring to the room.
Is this networking?
No. There are no pitches, referral quotas, or business-card exchanges. Members absolutely do business together - but relationships come first.
What happens at my first meeting?
You attend the actual Portland mastermind. You'll share dinner and drinks, meet the members, and participate in the conversation.
Is my first meeting really complimentary?
Yes. If you're approved, you're our guest.
What happens after I request an invitation?
Our Membership Director will briefly connect with you to learn about you and your business and make sure the chapter could be a strong mutual fit.
Get in the Right Room.
Come experience Speakeasy Mastermind at an upcoming Portland meeting.
No pressure. No obligation. Just come experience the room.
We put high-caliber entrepreneurs in the right room so they can grow faster, make better decisions, and never build alone.
