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#FoundertoFounder : The most important part of your grant application is your team - Omolara Sanni, cofounder, Midddleman
At Hustlebean, we help businesses grow revenue, using field sales agents. One of our key audiences are founders—and because we genuinely care about their journey, we launched something special: #FoundertoFounder.
#FoundertoFounder is exactly what it sounds like—a monthly series from Hustlebean where founders share real insights with other founders.
For the very first edition, I sat down with Omolara Sanni, co-founder of Midddleman, to talk about applying for grants as an early-stage founder. Midddleman is a fintech company helping ecommerce businesses in Africa trade easily with China.
In 2024 alone, Midddleman won five pitch competitions—and Omolara, the forward-facing founder, shares practical tips and lessons that can help you win too.
Enjoy the interview—and good luck with your next pitch.
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How are you doing, Omolara?
Yeah, I'm doing well.
How's it been at Midddleman so far?
It's been good, we thank God. We are pushing every day.
Okay, okay, awesome. Many companies often go straight to raising funds. What inspired you to go through the grant route?
Yeah, I think for most founders who go the grant route, it's not necessarily because we’re completely against taking investor money. It’s more about timing—raising from investors takes time.
It’s rarely something you can wrap up in a month or two. In fact, there are certain times of the year when VCs aren’t even active—like two or three months when everything just slows down. So for us, it didn’t make sense to rely solely on that path.
That’s why we leaned into grants. And of course, there’s the obvious upside: it’s free money. Investors will always take equity, but with grants, you don’t have to give up any ownership.
You get to keep 100% of your company, and still have capital to run the business, invest in marketing, and move things forward.
That actually makes a lot of sense. You had an incredible run in 2024—I saw that you had 5 pitch wins in one year. Was there a moment where you felt like, “Okay, we’ve figured this out” or was it more of a slow build?
So I think it was a case of – we did not start applying until we were very confident about what we were practicing.
Ohhhh
So, the very first pitch competition I won was WETECH, and I remember that back in October of 2023, when Midddleman had just launched, I attended the first edition of that competition in December.
I didn't even know that it was going to be a pitch competition. I just thought that it was going to be like a conference, a tech conference for women. But I saw that women were pitching, and the winner got a grant.
And I was like, oh, ‘I would really love to be on that stage next year’. So that sort of gave us time to build the product, gain traction.
I feel like if we had started immediately, say when we launched in October, we would have gotten a lot of rejections.
It’s not that we don't get rejections now, but it's a little better because we have something to show for it.
We have traction. You can see that we're putting in the work, and this is something that is working. We have a solid product, solid traction, and a solid story.
That’s a great perspective. Most people just, you know, figure it out as they go.
I saw one of your tweets about how you’ve gotten better at pitching. How do you typically prepare—what's the first thing you focus on?
I think it’s really a combination of things, but the pitch deck is definitely key. I like to refine each deck to match the specific competition—I never just submit the same one everywhere.
Some competitions are strict—they’ll say the deck must not exceed 10 pages. So you have to find a way to tell your story, include the right metrics, and highlight the key numbers within those constraints. Others are more flexible, so you can go all out and share as much detail as you want.
So the first step for me is always to tailor the pitch deck for that specific opportunity. Then, I go on to write a script based on that version of the deck. It helps me stay clear, confident, and aligned with the story I want to tell.
Hmm.
The mistake many founders make is trying to freestyle their pitch because, of course, they are the founders. They feel like they can talk about their products and what they've built any time.
But pitch competitions are structured. You have to follow a particular structure – talk about the problem, solution, market size, and all of that.
So I try to write the script out , and then practice it. I practice with myself, practice with my co-founder, practice with friends. I get their feedback.
Am I speaking too fast? Am I speaking too slowly? At the end of my pitch, do you really understand what we do?
Interesting
Because, like, the worst thing that can happen to you during a competition is for you to go on and on and on, and then the judge is like, ‘Okay, so what do you guys do?’
It means that you've used too many buzzwords and you've done a bad job at communicating exactly what you guys do.
So simplicity is also very important. There's no need to sound technical or try to ‘sound smart’, but you get the gist?
Yeah I do.
I also practice based on the time that I’ll be given
Some give two minutes but I've also had pitch competitions that gave us up to four minutes, five minutes to pitch.
Another important thing that I do is to research the judges. So most of the competitions will let you know who the judges are, ahead of time, so you can do your research and just try to see what they are about.
A lot of them are actually VCs—or at least people who work in venture capital—so I try to prepare accordingly. Especially if they’re specialized in my industry, I know they’ll have very specific questions. It’s their domain.
I make a point to research them ahead of time—especially those who are active online. If they post often on LinkedIn or write blog posts, I read through those to get a sense of their thinking.
That way, I can anticipate the kind of questions they might ask and practice my responses.
I think having gone through a few of these conversations now also helps. The more you do them, the more you start to recognize patterns in the questions, and that makes it easier to stay confident and clear when answering.
That's fascinating. So in a way we can say that it’s like preparing for a job interview. ‘Cause that's what I do when I'm preparing for job interviews. I research the interviewers.
Yeah (chuckles)
Interesting. Okay, so what would you say is the most important part of a strong application? Is it the business model or impact that the company has made?
I think the most important, especially at the early stage, is the team. You have to do a very good job of showing them that your team is the best to execute the project.
Highlight your expertise. What you’ve done in the industry.
My co-founder and I have been in the e-commerce business before we started Midddleman so we really understand the market and have the experience.
We also have engineers who have spent their entire careers building fintech products. That depth of experience really shows—they’re incredibly good at what they do. So we make sure to highlight that as well.
So, I would say the team and then the traction.
Investors want to see that you've achieved something.
No one is backing ideas anymore.
Even if the product is not ready, there are some things that you can show as traction.
100 people in your waitlist, for example. Or you're secured important partnerships that will help scale the product whenever you launch.
So, yeah, there just has to be traction, something to show that you're making progress and that it is something that people actually want.
This is insightful.
Let me add one more. I think another thing is, the market size. People want to see how big this can get. The potential of the business.
Can I ask what your rejection to acceptance ratio has been like, over the past year?
I'd say like 50:50, so , say we apply to 4 competitions, we get into 2
And then there are a lot of near-wins . Getting to the semi finals but not winning. Those ones are more painful than the actual rejections.
Which was the most painful, and in retrospect, what do you think you could have done better?
Okay, um, it was the Aurora Awards by Indrive. There were 2,018 applications, we made the top 100 and top 30 lists but after that, we didn’t progress to the top 10.
It was really painful because, to have gotten that far, I was really hoping to get to the finals.
But when I saw the list of the companies that made it to the finals, I sort of understood why I didn't make it.
And that was because the award was very impact-driven. I think that we did a very terrible job communicating the impact of the product.
They wanted to see, beyond revenue, the impact of the business on the users.
And it's not like ours wasn't making that impact, we just didn’t do a good job at really communicating it.
I also think a lot of founders don't think they are making an impact. If you really do an introspection, there's an impact your business makes.
It's not just about making money but also about how you’re making life easier for your users.
So, yeah, I learnt that. I still even plan to apply this year to be honest.
Good luck with that . Okay, so now I'm curious. Where do you usually find these grant opportunities? Can I just do a Google search and I'll just find them or how does it work?
Oh, yeah, yeah, you can definitely do a Google search to find them.
But there are websites as well. Like opportunitiesdesk.org
And also, I belong to different groups and communities of founders where these opportunities are shared.
It also depends on what your social media algorithm looks like.
Really?
Yeah, at some point last year,the algorithm was showing me various opportunities.
Also, informing people helps. The Zenith bank competition last year?
I think up to 10 people sent me that link.
Wow.
Yeah, Linkedin as well. There are a lot of them on Linkedin.
Thank you for that. I’ve noticed that you do more of the forward-facing pitches, than your co-founder. What would you advise a sole founder who’s not the forward-facing type?
To be honest, they should definitely find a forward-facing co-founder
(Both chuckle)
But I mean, I also did not know I could do these competitions initially. I was more comfortable doing virtual pitches.
But the very first one happened to be for women so it made sense that I did it.
And because I won, it just made sense that I did the subsequent ones.
Adeola represents Midddleman too, though he’s not done competitions per se.
Oh, okay. Cool. With all the traction you’ve built, what’s next? Are you exploring other funding paths or staying in the grant lane for now?
It’s both for us, to be honest. We’ve never stopped trying to raise investor funds. We still speak to investors. But the free money, like I said, is very sweet.
I'm never going to stop going after that.
However, there’s a limit to the number of grants you can apply for to actually scale and build the kind of business you want. So it’s both for us.
