Failure Report
What I learned from my Q2 2021 business failures
The following is my attempt at sharing two of the most important failures from April through June 30 2021 for Duplessy Foundation.
It’s a way of holding myself accountable and showing an honest look at what goes wrong in leading an organization.
What is Duplessy Foundation?
We are a nonprofit organization that teaches women, immigrant, and minority business owners how to implement their sales process. Our vision is to help 1,000 diverse biz owners reach $1M per year by 2040.
What were our goals for Q2 2021?
Goal 1 — Successfully execute our 12 week Sales Accelerator Program
We wanted to help our group of women, immigrant, and minority business owners successfully complete our Sales Accelerator program. The program focuses on doing the important, messy work of installing a systematic sales process.
Here were our success measures:
Weekly Sales Activity
- Outreach messages
- Meetings booked
- Deals
- Revenue
We also hired various contractors to work on different parts of their sales process.
Researchers (compiling lists of partners and potential customers)
Graphic designers (creating sales materials)
Outreachers (sending messages to potential customers and partners)
Virtual assistants (admin work, project management, and getting organized)
Ads specialists (setting up paid ads for Google and Facebook)
The contractors served as a forcing function in getting our diverse business owners’ sales processes to become more systematic.
Goal 2— Raise $100,000 from 2 people
We received a generous matching commitment of $100,000. That meant in order to receive the $100k, we need to fundraise another $100k first.
While I have been part of selling $1M+ projects, this was different. This was selling myself.
The intent of these funds is to grow our organization’s capacity. We can serve more women, immigrant, and minority business owners across the US. We can invest in sales materials that will help us attract referral partners with bigger budgets.
We can grow from 20 Accelerator program participants to 100 per year. We can increase the number of diverse business owners who receive sales coaching outside the Accelerator program from 100 to 1,000 diverse business owners per year.
Failure #1 — I Failed to Raise $100,000
Three big reasons why this didn’t happen.
🤞Reason A — Not enough trust
Honestly, the lack of trust went 2 ways.
- I didn’t trust myself enough
- I didn’t build enough trust with my potential donors
I’ve successfully sold big projects for companies where I have worked as a consultant. Selling this organization, (my baby) is too personal.
A lot of times I am thinking,
“Your wins are from 2020, do you think anyone will care?”
“You need more case studies to prove you are credible.”
“Your deck needs more work”
I didn’t feel really confident pitching the organization until our recent program cycle ended.
Special thanks goes to Katherine Kennedy for helping me craft a meaningful pitch. 💖
Building trust with potential donors is a different story. Taking the time to cultivate the donor relationships and build the trust took a backseat to other relationships.
Relationships — Level 1: The people we serve
This past three months my main focus was on the group of diverse small business owners participating in our Accelerator program. I taught two 2 hour sessions per week for 3 months. I also met with the 15+ individual diverse business owners outside of class all the time.
Relationships — Level 2: Referral Partners + Coaching Partners
My relationships with our referral partners were just underneath our business owners. In our model, the small business owners we teach are not our paying customer. It’s the community based lenders called CDFIs who refer the business owners to us.
We were building trust with referral partners by meeting with business owners other than our program participants. Every week we are chatting with referral partners about different aspects of our program.
Our coaching partners HubSpot and Acceleration Partners were the other relationships we were cultivating. We’ve had close to 40 HubSpotters volunteer for our workshops. Some of Acceleration Partners’ best people took time to mentor our ecommerce biz owners for 4 weeks.
It’s been a tremendous boon for us to have the experts who work in different sales channels provide direct service.
Relationships — Level 3: Potential Donors
Potential donors’ relationship with me and Duplessy Foundation were the relationships with the least focus. Part of it was taking time to craft the pitch. The other part was trusting myself enough to figure out an authentic way to build relationships with people who get pitched all the time.
⏳Reason B — Not enough time dedicated to the task
Tracking my time for Q2, I can see where most of the time went.
This past three months my main focus was on the group of diverse small business owners participating in our Accelerator program.
Officially, 104 hours 19minutes and 31seconds went towards the Accelerator program.
Pretty sure 80 or so hours that were not credited to the Accelerator could be tacked on.
I taught two 2 hour sessions per week for 3 months. I also met with the 15+ individual diverse business owners all the time. I also taught separate workshops for our current and future referral partners.
There are probably 10 people in my network who could donate $50,000. If I spent 3–5 hours with them cultivating the relationship and building credibility, there is a good chance 1 of them would donate.
🧲Reason C — Not enough outreach to potential donors
Math is a beautiful thing.
100 people in my network receive an outreach message from me.
25 respond.
10 have suggestions and make intros.
2–3 of those conversations get serious.
If I am writing thoughtful notes to each person this is 2–3 days of work. The key is that I focus on nothing else.
👶 The Baby Disclaimer
For the uninitiated, I was taking care of my 14 month old son the past 6 months. His care cuts my regular work hours in half.
God bless any person trying to run an organization with a new baby.
The outreach didn’t happen because it wasn’t scheduled and it was a priority.
In the future, I am going to focus my brain power on one major project at a time.
My inclination to refine our program model, go deep on relationships related to the day to day work, and take care of my son was good.
Attempting to fundraise at the same time as developing our program infrastructure was a failing proposition.
The FIX: Aim for a much bigger fundraising goal.
A recent conversation with a mentor changed my perspective. He’s raised a billion dollars with a capital B. He kept mentioning millions as a starting point for fundraising. It made sense to now target millions myself.
If I want to raise capital, it should cover the cost of growing over 3–5 years. Failing to raise $2M could get us to $1.2M. That kind of money allows us to focus our attention on building infrastructure for our program and growing to serve more people.
Failure #2 — I Failed to execute all the Accelerator program ambitions
Here is a quick summary of our Accelerator program. 12 Weeks of coaching diverse business owners on implementing and executing their sales process. The group meets Wednesdays and Thursdays for 2 hour work sessions.
Most of the diverse biz owners are either B2B or Ecommerce businesses generating between $1,000 and $20,000 in monthly revenue.
We spent $15,000+ on contractors to help the biz owners execute or improve their sales process.
There were 2 category of failures for our Accelerator program
- Stuff we planned to execute
- Stuff we found out we needed to execute
Stuff we planned to execute
50 Outreach messages per week
Our intention was for each participant in the Accelerator program to send 50 messages to potential partners or customers every week. A simple way of doing it is 10 outreach messages per weekday.
The challenge with this plan is people are motivated to do something when they see feedback. When most of the messages went unanswered, many participants were discouraged. Beyond that, we also had the issue of doing the necessary research so the outreach was actually targeted. Developing those lists takes time and energy we should have planned for — even if we executed less of our curriculum.
Every week we asked the participants to fill out a “Sales Activity Sheet” to measure their activity. It was a great accountability tool for the end of the week. Consistently, the outreach numbers averaged below 50 per week.
The FIX: Make outreach a game
Next time we will start each Accelerator session by asking participants to send 5 outreach messages. We are also going to celebrate when participants go outside their comfort zone with their outreach. Then we will help them develop lists, scripts, and workflows to get the outreach done quickly.
Systematic and regular outreach is a mindset that has to be cultivated.
Structured 10–15 minute slideshow presentations
The Accelerator sessions usually started with a presentation to demonstrate a concept. The quality of those presentations varied greatly. Sometimes I had 15–20 slides, other times I picked someone to be a case study or worse, I was just talking my way through the concept with zero visuals.
The effect was certain concepts clicked — and others didn’t. When the concept resonates and we are able to turn that into action, I was overjoyed. Concepts that did not click right away were inconsistently applied. I had to take more time explaining them again to the people who are visual or need a concrete example.
Ideally, this is the flow of a session:
Phase 1
5 min warm up activity
10 min concept explanation
10 min worksheet/small group discussion/
Phase 2
15 min live case study
15 min Q+A
Phase 3
45 min application of the concept
15 min Questions + next steps
If the presentation portion goes 30 mins or 1 hour, we are limited in the application portion of the session.
One thing I have learned is teaching via demonstration and application are a key part of our ‘secret sauce’. My intention is to make sure both are being used effectively.
The FIX: Prepare all 24 presentations in advance
The first 4 will be fun. The last 20 might be the devil to produce. The benefit of designing all the classes at once still outweighs the cost. Even if we have to make an adjustment reacting to the Accelerator cohort, we can share the presentations before or after the sessions via video.
Setting up CEO mentors
We were supposed to setup conversations between our Accelerator participants and CEOs generating 3–5 times their revenue. I thought we could setup these conversations 8 weeks into the program. That was way too late to reach out to people who don’t know me for a favor.
The funny thing is none of the Accelerator participants are heartbroken about CEO mentoring sessions. They found a lot of value in other parts of the experience. They like the application of the concepts, hiring contractors to run different parts of their sales process, and the community they’ve built with each other.
In my quest to add value, it might be better to remove parts of the experience. We shall see.
The FIX: Reach out to the CEO Mentors on Week 1
Stuff we found out we needed to execute
Weekly qualitative progress reports
Every week the Accelerator participants receive a report with their outreach messages, meetings, and deals. The report also has revenue numbers. It’s a great snapshot of their sales activity.
What we didn’t have is the qualitative equivalent. Numbers can tell you how you are doing in a week. They didn’t paint a full picture of what to do in response to the results.
The FIX: Add qualitative questions to our feedback loop
Creating a sense of momentum with our Accelerator cohort is about a communication rhythm. That rhythm feels like a weekly qualitative assessment participants fill out with progress, problems, and potential plans. Then a response sent on Sunday to help implement solutions that improve their sales process by changing their systems.
CRM
Our cohort kept track of their sales conversations via sticky note or not at all. 0.0% of them were using a CRM prior to starting the program. It was like watching a basketball game and only seeing the final score at the end. There was no way of understanding the progress of one deal or any deals in their pipeline.
It was clear that most CRM companies were intimidating to our small business owners. So many features. So many integrations and ways to get fancy. We needed a set of exercises to help our cohort ramp up to regular use of a CRM.
The FIX: Add CRM lessons to our curriculum
Practically, getting our diverse biz owners to focus on moving their top 10 potential customers/clients/ partners through a sales process will be enough. They can take notes and track significant sales developments in one place.
If we get fancy, I would love to incorporate HubSpot and LinkedIn volunteers to help our biz owners navigate their platforms. HubSpot CRM is free with many advanced features. LinkedIn Sales Navigator is a great tool to help identify potential partners and customers. These measures will have to be implemented from the beginning of the program.
Final Thoughts
Writing a failure report is a great exercise. I encourage you to write one to externalize what’s not working in your organization and why. My goal is to write these failure reports quarterly to share what I am learning and hold myself accountable. Hopefully, you learn something in the process and try it yourself.
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Duplessy Foundation is a 501c3 nonprofit that teaches women, immigrant and minority entrepreneurs how to implement their sales process. Our goal is to coach 1,000 new women, immigrant, and minority biz owners to $1M per year by 2040.
