My name is Jake — CEO and Co-founder at Pepper. 

Pepper is a social recipe-sharing application — which helps you share your recipes with friends and family. 

Our vision is to support cooking creators worldwide by helping them monetize their business, build their brands, and share their passion for cooking with the people they care about.

We kicked off fundraising about 3 weeks ago that we’re hoping to close it by the end of this month.

We're currently in the diligence phase — close to selecting our lead investor. We'll then sort out the rest with the follow-on interest that we have lined up.

My fundraising approach was different in the past — It’s important to acknowledge that I was a first-time founder.

I started with $40k from friends and family at a $500k valuation. From there I kept raising in small chunks as our product hit new benchmarks.

We’ve managed to raise a little over $1M through various SAFE notes over 2.5 years — we were about to gradually bump up our valuation with each funding round. 

It was a learning curve, but it set the stage for this current round.

We determined how much to raise by projecting 24 months of runway and then adding about 50% on top of that — you'll always need more than you think. 

We decided to raise funds while we were still in a comfortable financial position, anticipating that financial flexibility would help us navigate upcoming obstacles.

It's much harder to raise when you need to, rather than when you are able to. We raised at a valuation that the market deemed fair.

If no one is investing, it means your valuation is too high. If everyone wants to invest, it means you're too low — the market is always right.

Our primary goal with the money raised has always centered around achieving key milestones.

Since we're a consumer social platform, these milestones have focused on benchmarks like community size and product development.

For our first raise, the top priority was to launch in the App Store and gain traction. Once we did, we secured tens of thousands of downloads and attracted more interest from angel investors.

With that momentum, our next goal was to grow our user base to 100k. After achieving this, it became clear that we needed to build out monetization features.

We then started developing revenue streams on top of our community. Now that we've scaled to 1M users, we're focusing on expanding the revenue streams that have proven successful.

We are concentrating on our new consumer subscription, our media arm, and our grocery shopping integration.

This current round is crucial because it allows us to delve deeper into monetization features.

By the end of this round, we aim to reach around $3M in MRR. Achieving this would be a significant validation of our strategy and potential.

Much of our early funding came from friends and family — we didn’t really have the luxury of choosing between venture funds.  

While these initial checks weren’t necessarily strategic, having an investor who supports you from the sidelines can still be very valuable.

Alignment is the single most important factor.

If you can find them, strategic investors with connections — those who can get you featured in press releases or help you raise more funding — can make a huge difference in a startup's success."

It was really tough. It’s honestly about doing the hard work and putting in the effort to get as many introductions as possible from people you already know. From there, the word begins to spread.

We didn’t close any checks until we were live in the App Store with solid traction. People then started hearing about us — creating a domino effect.

One creator would post about us, and suddenly we’d get 5k downloads, another post would lead to 10k more.

I see it as a snowball effect. If you want to roll a snowball down a hill, you have to pack it yourself first.

For us, that initial packing was a constant effort to put ourselves out there, which is crucial for a consumer app.

We were continuously shipping content, saying, 'Hey, we're still here. We're still growing.' Eventually, that outbound effort turned into inbound interest, and investors started coming to us — the traction did most of the work.

I've likely taken close to 500 meetings, realistically, it feels more like a thousand. 

Our email list has around 200 contacts that we’ve kept in touch with. 

This approach helps us stay top of mind as a consumer-focused company. We currently have about 30 investors, all of whom are angels; we haven't pursued institutional investors yet.

In our current fundraising process, we've had around 60 introductory calls. These weren't cold calls but rather introductory discussions with people we've built relationships with over the past 2 years.

We used these calls to update them on our progress, share what we're doing, and outline our future direction, inviting them to join the conversation.

From there we narrowed down the group to those who have vetted our data room — we're hoping to receive a few offers that will help us decide the best path forward.

It was about being authentic and leveraging our strengths.

Early-stage investors are primarily investing in you and the team — not just the current product. These investors know that you’ll likely pivot the business in some shape or form.

I pitched my background and our team's strengths, focusing on the fact that on top of our product being great, the team's ability to execute and adapt was just as impressive. 

Pitching yourself as a founder is equally important as pitching the business.

When it came to metrics we pitched typical consumer ones like customer retention, monthly active users, and engagement metrics such as posts and saves. 

These painted the best picture of the growth we were seeing at the time. We currently have nearly 100k recipes on Pepper and just surpassed the 1M download mark :)

We didn’t really have a specific strategy here. The biggest thing is to not take rejection personally — I've been rejected around 500 times.

It's not about you or your company — sometimes the opportunity just isn't right.

If it's meant to be you'll stay connected to those investors. You can pull out that investor rejection folder you've been keeping and show them how you've built an unbelievable company.

A wise man once told me something that stuck with me.

He told me one thing he really looks at when vetting founders is how they manage cash. 

His point was simple: when you have a lot of cash, it can burn a hole in your pocket fast, and once it's gone, it's tough to find more because investors start keeping their distance.

We've been fortunate enough to be lean and flexible — we're now very comfortable when it comes to financing, but that wasn't always the case. 

Almost all of our competitors that popped up in the last two years has folded because of cash management issues.

Cash management is going to be the single greatest obstacle for a lot of founders. If you can maneuver it intelligently, you’re going to be successful.

I was chosen as a contestant on Gordon Ramsay’s Food Stars on behalf of my company. 

I went through several weeks of challenges with him, including winning Week 1 where I helped serve food on a beach. 

One of the funniest experiences from the show was during the first episode — Gordon had me unbutton my top two buttons because he said I looked too serious. 

I told him I’m a tech founder, I usually never have this many buttons! See tweet.

Everyone's experience is unique. We did what we had to do and I wouldn't change it — it simply couldn't have been done differently. 

No one's journey is straightforward; it will shape you and become a valuable part of your story.

No matter what it’ll become an amazing battle scar for you and your future.

Tom & Scott from FC Centripetal were my first true advisors. They have the experience to give hands-on support for everything I throw at them. I would start any company with them by my side.

I recommend reading the book "Secrets of Sand Hill Road." It’s written by one of the first employees at Andreessen Horowitz. 

While it may not directly give you advice on how to raise, it does explain the dynamics that exist such as understanding who your investors’ LPs are and why that’s important for you. 

It’ll help you really understand how you want to be framing yourself as a founder.