I’ve won plenty—but lost even more. Here are some of the mistakes I made so that you can laugh at me and try to avoid repeating them.

1. Requested a budget increase. Grantor felt stabbed in the back.

In the due diligence meeting the funder said of the 18 companies that had reached due diligence before they had funded 16. It would really be hard to lose this grant. After the call the entrepreneur said they could really do a lot if we doubled the budget. I didn’t see any issue with that since we would more than double the impact. After receiving our updated budget the funder said they didn’t feel comfortable with the budget increase. Then they ghosted. And that’s how I lost $500k.

2. Failed to hit the final submit button.

When I followed up 6 months later to see why we hadn’t heard back the funder said they hadn’t received our application—we had never hit the final submit button.

Now a writer's job is not done until they take a screenshot of the confirmation page

This helped us 2 years later when a grantor said they hadn’t received our application. We showed them the screenshot and they realized it was their error. We were ultimately awarded the grant.

3. No local experience

When I first started my work in Africa I pitched at a business plan competition with no previous experience setting foot on the continent. And, big surprise, won nothing.

But the enthusiasm was enough, apparently, and someone in the audience anonymously gave me $5k.

4. Insufficient Risk Analysis.

We scored 4 out of 10 on the risk assessment section of the grant due to listing only 5 risks which perhaps dragged our application down and out of contention.

5. Wrong color skin.

We were awarded the grant initially, but the funder wanted to fund Africans (in an email they accidentally cc’d me on), and the foreign-born entrepreneur was ultimately rejected.

Double-check previous investees to see if they are all black/women and adjust accordingly.

6. No track record or plan to implement

We deserved to lose that one.

Now we make sure the entrepreneur at least has a successful pilot of 6 months and/or 50 users before applying. At least submit a 3-phase plan to implement in the concept note.

7. The entrepreneur paid too early for expenses

The entrepreneur received a phone call saying, “We plan on awarding you the grant.” The contract wasn’t signed until 9 months later. By then, the overeager entrepreneur had already paid for the project-related costs, assuming they could be reimbursed.

They could not. All of the project expenses were deemed ineligible.

8. Applied from a manufacturer instead of a retailer.

The funder wanted money to go to a company directly in contact with the end user.

Write grants for organizations that are as close to the action as possible.

9. Wasn’t able to close the entrepreneur.

I couldn’t convince the entrepreneur that we had a good chance of winning even though it was almost a sure thing: the entrepreneur was a perfect fit and it was not a competitive grant. They didn’t apply on their own either. Everyone lost.

I think the entrepreneur’s heart wasn’t in the game anymore. I heard a year later they had wound down their biz.

10. More competitive than Harvard.

Applied to a prize where there would be 5 winners. Later, I discovered there were 2,750 applicants. Thus, no matter how good our application was, we were unlikely to win.

We don’t apply there anymore.

11. Entrepreneur Delay

During due diligence for funding that was already allocated to us, the entrepreneur took 3 months to get detailed quotes to put our final budget together. The funder pushed us to submit quickly but by the time we sent in the final budget, the funder had run out of funds to disburse.

Already have a detailed budget with quotations before applying.

12. Entrepreneur failed to draw down on the money.

After they won $120k, the entrepreneur just never made use of it because they needed certain marketing skills that they didn’t have.

13. System overload

We planned to submit earlier but the co-applicant partners kept delaying their parts of the submission. Finally, we were submitting 1 hour before the deadline, and the funder’s system kept crashing due to the load. We couldn’t submit before the deadline. We were a favorite to win but the funder said “rules are rules” and we were disqualified.

Submit the day before the deadline.

I hope that helped and made you laugh.

Do you know someone who would find these failures cathartic? Please share with them.

I had an interesting call with a contractor today. I said "you're really good at the numbers/analytical side but there are two sides to this: Numbers and emotion/storytelling. If you were as good at the storytelling as the numbers I'd pay you twice as much. And if I'd pay you twice as much I suspect any other employer would too." The contractor seemed to be very surprised. "Really? Can I bring this up in the future when I want a pay raise?" "Absolutely. I'm looking high and low for people who can do both numbers and storytelling." 

Is this surprising for you to know? I'd be interested to find out. Maybe I haven't communicated the need to tell stories well enough (for other contractors they have the most room to grow on the numbers side, but that's for another post). And of course Numbers+Stories isn't everything you need: the trifecta of any candidate is skills (in this case numbers+stories), work-ethic/energy/enthusiasm and integrity. The bare minimum is skills. But without work ethic all the skills aren't put to use. But integrity is the most important. A person with skills, work ethic and no integrity is a dangerous person that I run away from.

But back to the point. This contractor could double their pay in 6 months if they put their mind to it. Or it might take 10 years (or never happen) if they don't.

But all this philosophizing does you no good without some course of action so I'll tell you that right now.

Here are a few things to read that will change the way you tell stories (and yes, if you apply them, double your pay at the very least--not only will your base pay rise, but you'll win more funding which is money in your bank)

• Strategic Storytelling (book, focuses on The Pyramid Principle)

• Most persuasive story ever told (blog)

• The Elements of Style

• On Writing

• A Swim in the Pond in the Rain (book, deconstructing Russian Novels)

• Plotting vs. Pantsing in Game of Thrones (Twitter Thread)

• Archetypal Story Structure

But ultimately there is one key to being a better storyteller: write more.

I hope this helps you. If you know someone this could benefit please share with them. And see our jobs at thegrant.co/jobs.

Yours, Kyle

[Our full thread here]

If you haven’t heard, OpenAI (the Elon Musk founded AI startup) just released a new feature called ChatGPT. You can ask it write a poem about hotwiring a car…and it will:

The question for is, can it raise money?

I asked ChatGPT questions:

• on how to cold email an investor and

• from in a recent $1.7m grant we won

here are the answers:

How to cold-email an investor:

Do a market analysis:

Create a Risk Analysis:

How will this project be sustainable when the subsidy ends:

What are the barriers to solar in Nigeria:

Is it better than a human?

I’ll let you be the judge. Try this quiz with 3 answers by GPT and 3 by a human. See if you can tell which is which :D And try to rank each response to see which is better. Good luck!

See our whole thread on twitter here on other funding questions it can answer.

Update:

Here’s a tool that helps with grant writing called Grantable