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Sponsorship: How To Get My Money

By In Sponsorships, Startups

Getting a sponsorship isn’t THAT difficult. Over the last three years, I’ve sponsored a large number of local, national, and international events. My company mainly sponsors causes that are close to my heart as well as my business. This means startup community events, tech competitions, mobile app development conferences, etc. The problem is that the types of requests I’ve received from organizations have been so unbelievably poor that I’ve turned some of the requesters into whimpering piles of PTSD. I’m not a mean person by nature. If you’re going to ask me for money, please put a little time and professionalism into your request. I know that most of the people that are forced to handle these requests can be a little green, but an ounce of training, or a decent template, could go a long way to settling my annoyance.

So, here are a few tips based on some of the most egregious faux pas I’ve had to deal with.

1 .Start with the people or companies that gave last time

I’m not sure why, but I’ve heard a number of times something similar to this:

“Well, I didn’t contact you first, because you were really generous last year, and I didn’t want to bother you.”

That’s so unreasonable, I cannot begin to imagine the mindset. This can only come from eating too many crayons as a child. The entire value proposition to a company in sponsoring an event or institution is marketing exposure. Yes, you give to the events and organizations you believe in, and there is a feel-good charity aspect as well. But all the feel-good reasons in the world are not going to get anything but the largest companies to sponsor you. This is an advertising play. The deal is simple: I want exposure, you are offering exposure. You’re not bothering me by giving me the offer to promote my business.

The second thing to remember here is that no one likes to be picked last. I have had a number of organizations contact me with my other pet peeve:

“Hey there, I know you were one of our main sponsorship partners last year, and I wanted to know if you could help out. We’re only $X away from meeting our goal, and I was hoping you could help us cross that finish line.”

Are they suggesting that the only reason we’re getting the offer is because they didn’t get enough money from their first choices? Am I to understand that you’re scraping the bottom of your funding barrel with your email? No thanks.

2. Ask your sponsors to participate

Most of the types of events that I sponsor in the tech world have some sort of support role needs. These are things like being a mentor for young entrepreneurs, being a judge in a startup competition, or possibly being a guest speaker. What’s nice about this is it’s a little extra exposure; something your marketing people can write about how awesome their CEO is for helping out the little guy.

Other than the ego stroke, it is also really rewarding to help out. I feel good when I get to pass on some of the lessons I’ve learnt the hard way. I feel even better when I can steer someone into a new way of thinking that they had never considered.

Unfortunately here’s what happens: I show up at an event to which we’re the premier sponsor, and the list of mentors, judges, or dishwashers includes a list of people who didn’t actually shell out cash, listed on the event’s website (usually above our company’s logo). Not to mention that I’m not sitting at an event, which I paid a lot of money for, and I’m not doing anything. I’m not a participant. I’m not a mentor, judge, or dog walker. What am I supposed to do? Write blog posts?

Get your sponsors involved. If they’ve got the cash to fund your event, they might know a little bit about whatever it is you’re doing and can help.

3. Don’t treat the offer to sponsor as a Noble Prize nomination

Here is another gem of an email I’ve gotten:

“Hey Greg, I’ve attached a document here to our event. It’s going to be huge, and I wanted to see if you would like to get in on this.”

The document you attached is targeted toward the attendees, not potential sponsors. It tells me nothing about how much money you’re looking for (I assume you’re looking for money, but I can’t tell from your email…), or what my money will go to, how it can help you, and what exposure I will get in return.

Look, I don’t need to be buttered-up to strike a check, but for heaven’s sake, there are wiki-how articles on this stuff. Due to the last five or poor sponsorship requests, I’ve gotten I’ve changed my sponsorship policy: If you’re looking for $100 or for me to buy your homemade cookies, this is fine. If you’re looking for $10k, then you probably need to show a level of professionalism that is a little more than “this is going to be huge — let me know if you want in.”

Look, this isn’t the worst request I’ve gotten (which is embarrassing to say the least), but it’s pretty bad. Maybe you have so much money coming in that you really don’t care. Or, as you imply, the event is so big that you have sponsors fighting over those last two spots like rabid Black Fridayers. But if either were the case, it would leave a bad taste in my mouth for the next time you came to ask for money.

This is a sales call. You want me to give you a sponsorship for something in return. Something as simple as, “We would love for you to be a sponsor” would go a long to preventing your evisceration.

4. Personalize your pitch

See above point. Don’t just attach the document you’re sending out to attendees. Make the offer about me.

I have had those emails to the masses just copied and pasted to me. The last guy who sent me something got a fairly unprofessional response from me (something I regret!) His implication was, “Hit me up if you think this is cool” which I don’t see working for anyone outside of high school.

Put my logo into the sponsorship document, mention how it will benefit us, talk about our companies previous events… anything. I’ve dropped huge sums on people who have actually mocked up what a stage will look like with our logo embossed over it, and I felt great about it. A little effort goes a long way.

Let me know exactly what you’re looking for; how much money, time, and anything else. Tell me what you think the benefits to sponsoring the event will be.

5. Call me for that sponsorship

This is somehow not obvious to people. I understand an email is easy, but this is a sale. Basic sales etiquette should apply. Pick up the phone, call me, and tell me you’re going to be sending me an email to follow up. Even better, email me asking me for a call or a meeting! The sponsorship is as good as yours.

6. Make good on your promises

I recently sponsored a gala at my alma mater, for the third year in a row. I’m a got a nice award from them one year. Why wouldn’t I sponsor? Well, last year their pitch was pretty good. They promised that our logo would be smeared over every wall and digital display, there would be a kind “thank you” on stage for our few dollars of assistance, we would have a full-page ad in the event booklet, and we’d receive some social media recognition. Not bad for a few thousand bucks.

What did we get? Not even a mention.

Every screen was blank, no one said a word on stage, and there wasn’t even an event booklet. To add insult to injury, we didn’t even get an apology after the fact, let alone a thank you email. So this is called a scam. This year I declined to sponsor, even though I believe in the cause. It’ll probably take me a year or so to stop being so angry. They might be able to get something out of me again in the future. Right now though, I’m just angry.

Don’t be like these people.

Try taking a look at PRHelper or Spark Templates for some examples of how to write a sponsorship letter. Or even that SEO dreamers Wikihow’s version. There is honestly no excuse to mess this up.

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I help companies turn their technical ideas into reality. CEO @Sourcetoad and @OnDeck. Author of Herding Cats and Coders. Fan of squash, whiskey, aggressive inline, and temperamental British sports cars.

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Don’t Fall Into the Trap: Why Startup Software Development Isn’t Like Corporate Development

In Startups, Technology

So, you’ve left the corporate world, and now it’s time to build your own startup. You’ve probably managed dev teams before, overseen product launches, maybe even helmed some fancy project management tools that made everything run like a well-oiled machine. You’ve done this before, right? Not exactly. When it’s your startup, everything changes—and, as I’ll explain, if you assume it’ll work the same way, you’re heading for a few surprises.

Startup founders often fall into a dangerous trap when starting a software project from scratch: thinking it’ll be just like building software inside an established company. Here’s why it’s not—and some advice on how to navigate the differences.

1. Switching from Product Manager to Teacher

In an established company, a software team already has two things that give them a serious edge: an existing market and a deep understanding of the business. They’re working within a proven model. Developers in that environment know what questions to ask, can fill in gaps intuitively, and likely understand why they’re building what they’re building.

At a startup, however, your devs are going to need a whole lot more context. They’re not working with familiar requirements—they’re working with your vision, which may be abstract at this stage. If your development team doesn’t understand why something matters, it’s a recipe for ambiguity and frustration on both sides.

Advice: Think of yourself less as a product manager and more as a teacher. Your job is to make sure they understand the core problems, not just the features. Teach them why each requirement matters, help them visualize the end-user, and create that shared language for decision-making. It might feel tedious, but it’s essential to avoid future misalignment and expensive rewrites.

2. Beware of Perfectionism — It’s the Budget Killer

In a large company, products with an existing user base often have to be polished. Features need to be rock-solid, invoices have to be perfect, and everything needs an audit trail. Startups, however, have a different goal: get an MVP in the hands of users fast. It’s a classic trap for first-time founders—focusing on “perfection” and “polish” before knowing if the business model even works.

Startup perfectionism is budget poison. It’s shocking how quickly adding “nice-to-have” features can chew through funding, especially if you’re paying a dev team to build things like automated invoicing or churn management before you’ve even proven people want what you’re selling.

Advice: Ruthlessly strip down your MVP. If a feature doesn’t help you validate your market, it goes on the “later” list. Keep the scope laser-focused on what helps you test your business assumptions. Let the non-essential features wait until you know you have customers who’ll use them.

3. Zen and the Art of the Startup Pivot

Building software for a startup means embracing one cold, hard truth: the business model will change. According to research, 93% of successful startups pivot at least once (and often more). Imagine being asked to go out and passionately sell something that you know might not look the same next year—or next month. It takes a level of zen acceptance that your original idea will likely morph, but that’s what keeps you flexible and ready to capture new opportunities.

For founders, that requires a mindset shift. You have to believe in your product, while also knowing you might be building the “wrong thing” in some way. The focus should be on preserving capital and brainpower for what’s next. The game is less about proving you’re right and more about staying adaptable.

Advice: Budget with pivots in mind. Set your burn rate assuming you’ll need to make big changes. Don’t let ego get in the way of listening to the market, and keep enough gas in the tank for at least one big strategic turn.

4. The Hard Work of Being Your Own “Internal Customer”

Here’s another big one. In a corporate environment, you have internal customers—departments or stakeholders with specific goals that align with the overall company mission. For a startup, the only customer you have is you. You don’t have a preexisting feedback loop from various departments, and you don’t have established success metrics. You have to create that from scratch.

Advice: Start by building an internal customer profile based on your target market, then use that to set clear goals and success criteria for your dev team. If you’re focused on, say, usability for early adopters, set KPIs around usability testing and build from there. By acting as your own “internal customer,” you’re setting a clear direction and saving your team from working in a vacuum.

5. Get Ready to Build AND Sell

Corporate software development often has the luxury of a separate, dedicated sales team to deliver the product to the right audience. As a startup founder, you’re both the builder and the seller. That means you’re not just iterating on software—you’re iterating on messaging, product-market fit, pricing, and maybe even distribution models.

Advice: Factor in time for sales-ready iteration in your dev cycle. As you build, keep track of how each release or update affects the user experience. Ask yourself if the changes make your pitch clearer or simpler and how they align with the current market’s needs. Ultimately, this approach will help you bridge the gap between building the product and ensuring it’s market-ready.

Conclusion

Building software as a startup founder requires a whole different toolkit than you may be used to. You’re part-teacher, part-salesperson, part-zen master, and always the chief budget officer. By recognizing the unique mindset shifts and traps of startup software development, you’re positioning yourself—and your team—for the best chance of success. Focus on creating clarity for your team, set ruthless priorities, embrace change, and never lose sight of the fact that the first version is just the beginning. In the startup world, adaptability isn’t just a skill—it’s the entire game.