My name is Kenan Saleh, and I’m a second-time founder based in NYC. I sold my first company to Lyft when I was 21 and I am currently building a new company in stealth. 

I also advise startups and run an investing syndicate on the side.

My first company was called Halo Cars. I founded it about five years ago. 

It was a rideshare advertising startup designed to enable Uber and Lyft drivers to earn extra money by displaying advertisements. 

We provided drivers with the necessary equipment, such as screens and other technology, to show ads on top of and inside their vehicles. 

We managed the ad marketplace, allowing drivers to generate passive income simply by equipping their cars with our technology and continuing their usual driving routines.

We sold the company to Lyft after about a year to help them kickstart their ads business.

We raised what could be classified as either a pre-seed or a seed round — raising $500k at a post-money valuation cap of $8M. 

The round started in May, right after the college semester ended, as we decided to transition from working on the project part-time as students to taking it on full-time.

The core period of active fundraising lasted about 1 to 2 months. The process was admittedly a bit tough as we were new to fundraising and hadn't fully mastered the strategy. 

Despite some initial challenges and learning as we went, we successfully closed the round in June. 

Just a few months later we sold the company — having signed the term sheet shortly after closing the funding round.

We decided it was the right time to fundraise based on a few things — we had decent traction, were super excited, and had a strong outlook for growth. 

We first focused on putting together a small pilot to build and test an MVP. 

This allowed us to demonstrate some traction — we had already generated revenue, secured a few paying customers, and established a small fleet of vehicles with advertisers satisfied with the results.

In terms of determining how much to raise and at what valuation, we started by setting clear milestones for what we needed to achieve with the funding.

We adopted a market-based approach — examining what was typical for pre-seed rounds, particularly looking at Y-Combinator companies and other startups from our university. 

This helped us establish a range that seemed reasonable in the current market environment. We were firm on the amount we needed but flexible on the valuation — letting the market ultimately determine what was right. 

This strategy ensured that we were prepared to negotiate but also ready to adapt based on investor feedback and market conditions.

The core goal for us was a growth milestone. We aimed to expand from Philadelphia to New York, grow our fleet to 150 cars, and reach $50k in MRR. 

These goals required specific resources, including additional hardware, payment for drivers — along with hiring sales, engineering, and operations staff.

We mapped out the costs associated with these needs and decided on a target of $500k to support our operations for 6 to 9 months. 

This amount was chosen based on our operational needs and the milestones we set to hit the next stage of growth.

In hindsight this was a pretty tight projection and could’ve used some more buffer.

We didn't initially have a complex strategy for vetting investors — it was more about grabbing any opportunity we could find. 

A lot of it came through introductions made by our university or personal networks.

The lead investor for our round was someone one of my co-founders knew from college who had just started his own venture fund. 

We focused on student funds that had been to our university multiple times —not having many initial options beyond that.

Our approach to finding the right investors was pretty simple and a bit of a learning curve since we were new to the whole startup scene. 

We started by connecting with investors linked to our university because they were accessible and often came to campus. 

We worked with student funds that were part of larger funds — like First Round Capital's Dorm Room Fund and General Catalyst's Rough Draft Ventures — because they had a track record of investing in student-led startups like ours.

Our method was about making use of the connections we had and meeting with anyone who was willing to talk to us — hoping they’d be interested in our idea. 

It wasn’t the most refined strategy, but it was our way of navigating things as first-timers in the startup world.

We started out not knowing many people in the investment world — we had about 15 to 20 pitch meetings in total. 

Of those around 10 were with serious venture capitalists — the rest were with angels or other individual investors.

The first month of pitching was tough — pretty much all rejections. 

Things suddenly shifted. We got our first 'yes,' which set off a chain reaction. After that we ended up with 3 more yes’s pretty quickly. 

It was a rough start, but that one positive response really turned things around for us — leading to competing offers and a much more optimistic situation.

In our pitches to investors, we really emphasized the big opportunity at hand — how we as a group of young, tech-savvy innovators, were set to shake up a pretty outdated market. 

We believed that by diving into this space, our company could become incredibly valuable.

Even though our product was still in the early stages, it had a bit of revenue — it was more of a proof of concept. 

The revenue we had was from a single customer — it wasn't something we could count on recurring yet. 

This was our way of showing potential, but making it clear we were still at the beginning of what we could achieve.

The real pitch was about us — the team — and the massive market opportunity we were eager to tackle. 

Our presentation was standard for a pre-seed stage startup. We walked investors through our deck, answered their questions, and tried to get them as excited about the potential as we were.

Nothing. We were students at the time so we focused on pitching ourselves and the market opportunity. We took whatever we could get.

The biggest hurdle we hit during our fundraising was finding a lead investor. 

It was especially tough because a lot of the pitches that felt like they went really well ended up with investors passing on the opportunity. 

Even though we had several investors interested in us, they all wanted someone else to lead the round.

This situation created a ton of uncertainty. There were moments when it looked like the whole thing might just not happen. 

We even started thinking about lowering the amount we were trying to raise as a backup plan. 

Right when we needed it most things turned around. Our last few pitches finally brought in that lead investor we were so desperate for. 

Once that happened, everything else snapped into place really quickly — we closed the round within a week.

In the closing stages of our fundraising, we ended up with some competing offers and it was pretty messy — I’ll explain how it worked.

Our lead investor put in $350k of the total $500k we were raising. Another investor contributed $100k, and an angel investor closed out the round with $50k. 

As we reached the end of the process, we had 3 serious potential leads.

One was from a group led by a person I knew from a pitch competition at our university — let’s call him the super angel. 

Another was a VC fund known for investing in ad tech — introduced to us by a classmate of my co-founder who had interned there.

The third was a solo GP who eventually led the round.

Each of these potential investors had different terms and approaches. 

The super angel had some restrictive terms that involved a lot of hands-on management and staged funding — this could interfere with how we ran the company. 

The ad tech VC was interested but was too slow to move forward. 

They couldn’t align with our timeline, which was crucial because we were eager to move to New York and start scaling.

Ultimately the solo GP who led the round was the most founder-friendly — respecting our valuation and was willing to invest under straightforward terms without undue oversight. 

His approach fit our needs perfectly — we were looking for hands-off investors who would trust us to run our business.

When it came time to communicate our decision, it was about being honest and respectful. 

We explained our reasoning to the other investors, focusing on the need for speed and less restrictive terms. 

This helped maintain good relationships, despite some investors not being part of this round.

If I had to boil it down to one essential piece of advice for new founders starting their fundraising journey, it would be — be persistent. 

If you have a deep conviction in what you're building, and you're ready to put in the work to meet investors, you will probably raise. 

Fundraising is fundamentally a numbers game combined with a lot of hustle.

You might find yourself pitching to a hundred different investors. It's essential to keep going despite the rejections. 

From my experience the sheer will to keep pushing forward makes all the difference. 

Some people might get discouraged and stop after a few rejections, but there are many more investors out there than you might initially think. 

The more people you reach out to, the better your chances of securing funding.

Stay persistent, keep your conviction strong, and keep reaching out. That’s how you'll maximize your chances of getting the funding you need.

Ran Makavy - he was the CPO of Lyft who led our acquisition.

He previously sold a company to FB and was their VP of Growth.

He’s an amazing operator, very well connected and respected, and the smartest executive I’ve ever met. He runs a solo GP fund now.

One is a strategy shared by a guy named Bruno in a tweet — he detailed how to line up investor meetings back-to-back to run a tight process. 

It’s a solid piece of advice because keeping your fundraising efforts compact can help maintain momentum and create a sense of demand among investors.

Another valuable resource is a book by Ryan Breslow. 

It focuses on how to build relationships with investors over time, which is crucial.

It's not just about the tactics of fundraising — it's about how you warm up potential investors before you even start the formal fundraising process. 

This includes having casual conversations, sharing updates about your progress, and then clearly signaling when you're ready to raise.

They were super excited to put it mildly. They really pushed us to go for it because it meant a quick, lucrative return on their investment. 

We were talking just a few months after they'd put their money in, and they were already seeing a solid multiple back — that's rare.

They were all for it right from the start. As soon as we mentioned we were considering the acquisition, they said, "Absolutely, go for it. Don’t mess this up." 

They saw it as a big win. Most of our investors were angels or smaller VCs — not the huge firms that might be used to frequent big exits. 

For them this deal was not just about the money coming back — it was a validation of their decision to back us in the first place.

They were thrilled because this was a chance for them to show their own backers that they pick winners.

This success could help them raise more money in the future or just boost their reputation as investors.