Calendar of Sessions
How do Prosperity Circles Work?
Prosperity Circles are as much about learning as about examining our own experiences and learning through others’. Each month, we’ll have a focus topic to help us learn and grow together. In the middle of the month, we’ll examine this topic up close with your businesses and have you present and share with each other. Then, we’ll wrap things up with a guest speaker. You can expect this general flow each month.
General monthly Format
WEEK 1: Focus topic introduction
WEEKS 2+3: Exercises and analysis of your businesses
WEEK 4: Guest speaker
All PC sessions are hosted at 12pm ET on Fridays.
see below for our proposed schedule of activities (subject to change).
June 2021
WHAT DO YOU WANT? KNOWING YOUR VISION
If you don’t know where you’re going, you’ll never get there. That’s why during our first month together we’ll spend time really looking at our vision — not just for our businesses, but also for ourselves. We’ll talk about where we see ourselves in the next year — AND the next 10 years. And we’ll get laser focused on what that looks like, so that we have a goal to move forward with.
WEEK 1 (4 June): Welcome to Prosperity Circle! At our first session together, we’ll go through the overall structure of how PC works, and introduce ourselves and our businesses. You’ll even get a tiny homework assignment (yup, I said homework) where we write up our visions for ourselves.
WEEK 2 (11 June): Exercises: Sharing our visions and getting feedback
WEEK 3 (18 June): Exercises: Sharing our visions and getting feedback
WEEK 4 (25 June): Guest Speaker:
COWORKING + REMOTE WORK ENTREPRENEUR AND VISIONARY NICOLE VASQUEZ
Nicole Vasquez honors the human component of business by seeking out individual perspectives, translating feedback into solutions, and collaborating across teams to deliver thoughtful, delightful experiences for customers, employees, and partners.
As the Chief People Officer of Deskpass, Nicole leverages her love for learning to continually improve the human side of company interactions: customer support, partner relationships, and employee engagement.
As a serial entrepreneur, Nicole has been named one of the “35 Under 35 Making an Impact in Chicago,” won the 46th Ward Innovator Award, the RedEye Chicago Big Idea Award for Community, and was a Professional Fellow through the U.S. Department of State traveling to Europe to speak about how to build and maintain collaborative communities.
When she’s not advocating for the freedom to choose where your best work happens, she travels, writes, and learns about the world by asking intriguing questions and having compelling conversations.
July 2021
PROBLEM GENERATION
Is your business a vitamin or a medicine? What exactly is the problem you’re trying to solve? Before we dive into our goals, we’re going to talk about our business — and make sure what we’re building is something that people not only want, but need.
This isn’t something you’ll likely figure out in a month, but by leaning into your customer personas and figuring out what they’re actually looking for, you can make some good assumptions on which you can start collecting data!
WEEK 1 (2 July): Problem generation, “jobs to be done” framework, and vitamin vs medicine. Homework: Interview 3 customers and start to hammer out what problems they have.
WEEK 2 (9 July): Exercises: Sharing our customer problems and getting feedback
WEEK 3 (16 July): Exercises: Sharing our customer problems and getting feedback
WEEK 4 (23 July): No circle
WEEK 5 (30 July): Guest speaker:
GEETIKA AGRAWAL, FOUNDER + CEO OF VACATION WITH AN ARTIST
Geetika Agrawal is Founder and CEO at Vacation with An Artist (VAWAA) - the first curated platform that enables anyone to book immersive mini-apprenticeships with master artists and craftspeople around the world. Her mission is to unlock profound human experiences that promote curiosity, deepen human connections, and preserve time-honored wisdom.
Prior to VAWAA, she was a Creative Director at R/GA leading product and experience design teams for brands like Lincoln Center for the Performing Arts, Mastercard, Disney, AARP. In 2015, she traveled for a year to 12 countries to build VAWAA and run an international traveling dinner series Food For Thought. Her work has won global awards and featured in leading publications like Skift, New York Times, Forbes, Travel + Leisure, VICE, Artsy, National Geographic and more. She has also served as an Adjunct Faculty at School of Visual Arts, New York and is a mentor/advisor to young talent.
A stubborn optimist, she believes that COVID is the positive reset our culture needed despite it's painful challenges.
Aug 2021
PRODUCT MARKET FIT + BUSINESS MODEL CANVAS
So, you have an idea of what you want to do. But does it fit the needs of the market and have you figured out how all the parts of the machine will work? This month, we’ll talk about product-market fit and spend some time sharpening our Business Model Canvases.
WEEK 1 (6 Aug): How to set reasonable goals for yourself and your business. Homework: Create 3 key goals for your business, and 2 goals for you, to accomplish by the end of this year.
WEEK 2 (13 Aug): Exercises: Sharing our goals and getting feedback
WEEK 3 (20 Aug): Exercises: Sharing our goals and getting feedback
WEEK 4 (27 Aug): Guest speaker:
INVESTOR, TRAVEL GURU + PRODUCT EXPERT SASHA HOFFMAN
Sasha Hoffman’s love of mobility, travel and automating archaic processes has guided her career from creating the world’s first cargo-carrying personal robot to leading IPOs for major technology companies. She's been to over 100 countries, delivered keynotes related to personal mobility, smart cities and travel tech at the WSJ Future of Everything Festival, Collision Conference, CES in Las Vegas, Phocuswright, Skift Global Forum and more, and has been featured in Wired, Bloomberg, WSJ, Boston Globe, UK's The Gadget Show, Fox, TechCrunch, and LSE Business Review.
She currently leads Customer Engagement at Uber where she's responsible for the company's subscriptions business, Uber Rewards and 3rd party loyalty partnership globally. Prior to that she spearheaded a new innovation division for Piaggio Group (makers of Vespa) called Piaggio Fast Forward. As Chief Operating Officer, she was tasked with creating new forms of transportation that utilized semi-autonomous functionality to better move people and goods around 21st century cities. With no prior experience in the industry, she designed and launched the world’s first consumer robot that follows a human carrying up to 45 pounds of cargo called Gita in under 1.5 years.
Prior to this Sasha was Head of Business Development for Plastiq, a fintech startup that raised $72.3mm of venture funding. Her interest in the technology sector stems from her time working as an investment banker in the technology groups of Goldman Sachs, Barclays Capital and Lehman Brothers where she worked on transactions worth more than $100 billion including several high-profile IPOs and M&A deals for such clients as Facebook, Yelp, and SanDisk.
Early in her career, Sasha created a travel company, worked for Gucci Group and helped start a handbag company in college that was launched on The Apprentice.
Specialties:
High-impact execution, loyalty programs, customer engagement, innovation strategy, startups, transportation, robotics, travel, human-robot interaction, personal mobility, rapidly scaling teams, business development, operations, mentoring, empowering and development of teams, smart cities, M&A, pivoting products
Sept 2021
TRANSLATING THAT VISION INTO GOAL SETTING
We’re in official 2022 planning season! We’ll use this month to set measurable, actionable goals that you can carry into 2022 to launch, relaunch, or grow those business plans.
WEEK 1 (3 Sept): How to set reasonable goals for yourself and your business. Homework: Create 3 key goals for your business, and 2 goals for you, to accomplish by the end of this year.
WEEK 2 (10 Sept): Exercises: Sharing our goals and getting feedback
WEEK 3 (17 Sept): Exercises: Sharing our goals and getting feedback
WEEK 4 (24 Sept): Guest speaker
“Recovering entrepreneur” and venture accelerator director Ashley Lucas
Ashley Lucas refers to herself as a “recovering entrepreneur” after having spent years working in the startup space, as a founder, a co-founder, and a venture accelerator director. Launching and leading her own digital media company that took her through the MassChallenge accelerator in 2010, Ashley was then recruited to co-lead a startup called The Welcoming Committee, a national events and travel company. There, she helped grow a Boston-based community of 2,000 into a membership base of 35,000 across ten cities. Four years later, she joined the team at Babson's Center for Women's Entrepreneurial Leadership (CWEL) as the Women Innovating Now (WIN) Lab venture accelerator director. Now, Ashley has switched gears, utilizing her entrepreneurial educator skills to build and launch a brand new Women’s Leadership Academy program that empowers women-identifying high school students to become more self-aware and confident leaders in their own lives.
Oct 2021
GROWING AN AUDIENCE
Before you can even create a sales funnel, you need to grow an audience that believes in what you believe. How do you do that, exactly? We’ll talk about audience growth tactics, favorite channels, and how to craft your unique message this month.
WEEK 1 (1 October): Let’s talk about audience.
WEEK 2 (8 October): Exercises + workshopping
WEEK 3 (15 October): Exercises + workshopping
WEEK 4 (22 October): Guest speaker: Justine Abigail Yu of Living Hyphen
WEEK 5 (29 October): BREAK!
PASSIONATE STORYTELLER AND ANTI-OPPRESSION ADVOCATE JUSTINE ABIGAIL YU
Justine Abigail Yu (she/her) is a communications and marketing strategist who has worked with organizations operating in North America, Central America, East Africa, and Southeast Asia. Her expertise lies in growing enterprises from the ground up through strategic digital marketing, compelling storytelling, and genuine community engagement through a lens of anti-oppression.
She is the Communications Director at Wanderful – a global travel and lifestyle brand that specializes in helping all women travel the world – as well as the Senior Advisor for RISE Travel Institute – a non-profit organization that promotes responsible, sustainable, and ethical travel through education. Justine is the Founder and Editor-in-Chief of Living Hyphen, an emerging magazine that explores the experiences of living in between cultures as a hyphenated Canadian – that is, an individual who calls Canada home but who has roots elsewhere.
Her work has been featured on national and local media outlets including the Globe & Mail, Yahoo! News, NextShark, and the CBC.
Justine Abigail is a fierce advocate for equity and anti-oppression. Her mission is to stir the conscience and spur social change. Learn more at www.justineabigail.com and www.livinghyphen.ca.
Nov 2021
CONVERSION FUNNELS
So, you’ve got your believers — but how do you turn them into buyers? This month we’ll talk all about conversion funnels and how we’re taking people to sale.
WEEK 1 (5 November): Let’s talk about conversion funnels. Homework: Write a three-email manifesto to your subscribers.
WEEK 2 (12 November): Exercises + workshopping
WEEK 3 (19 November): Exercises + workshopping
26 November: No PC (Thanksgiving)
WEEK 4 (3 DECEMBER): Guest speaker
SERIAL SOCIAL ENTREPRENEUR + ACTIVIST, global ADVENTURER + BRUTALLY HONEST STORYTELLER CAT JAFFEE
Catherine (Cat) Jaffee is an audio producer and writer. Cat started her career as a honey tour guide in Eastern Turkey, a Fulbright scholar documenting human migration in the Caucasus, a digital organizer in global climate movements, a PR Director for a big bank brand and a Communications Director for a cooperative grocery store. Then in 2017, she pivoted into audio when she founded House of Pod, a community recording studio and production company in Denver, as well as AMPED a non-profit that elevates marginalized voices in media. As a National Geographic Explorer and Storytelling Grantee, Cat wrote, recorded, and directed Guardians of the River, a podcast about one of Africa's most wild water systems, and the people who protect it. Completed while Cat fought a cancer diagnosis in 2020, Guardians of the River won best non-fiction podcast at both theTribeca Film Festival and the Jackson Wild film festival, topping the Apple Podcast charts as the #1 nature podcast of all time, and earning its name as an audience choice "cult favorite." Cat is also an ultra-bike packer and endurance racer, competing in the Silk Road Mountain Race in Kyrgyzstan as a Chumba athlete in 2021. She lives with her two border collies Maya and Mizu in Durango, Colorado.