How to Land Your First $500k Contract

Macy Mills explains how SR005's Anchr secured a big deal

Today we’re launching a16z speedrun Insiders: a high-signal community for enterprise innovation leaders who want early visibility into emerging AI products

We’ve already onboarded ~15 C-suite executives from Fortune 500 companies.

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💡 This Week’s Big Ideas

💰 SR003 alums TaleMonster Games announced their $30m Series A

🎉 Welcome Jackie Young, who just joined the SR team as our newest partner!

📋 We’re also hiring across a variety of functions. Jordan Mazer has the list.

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Today’s guest post is brought to you by Macy Mills, head of GTM for a16z speedrun. Be sure to follow her on LinkedIn and on X for more tips on GTM.

As Head of GTM at a16z speedrun, I get a front-row seat to founder-led sales. It’s the messy, unglamorous work of closing real revenue when you don’t yet have brand, proof points, or a big team. Every cohort, a few teams stand out to me because they do the basic things consistently and aggressively, even when it’s uncomfortable.

This is the story of one of those teams: Tzar and Smayan, co-founders of Anchr, an AI agent platform for food distributors (class of SR005). They’d set a stretch goal of $500,000 in booked revenue by the end of their time in speedrun. In the weeks that followed, the team secured a hard-won enterprise deal that allowed them to surpass that benchmark.

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The conference they weren’t invited to

Every industry has that conference—the one where the power players show up, and everyone else tries to get five minutes of face time. Food distribution has its own version, an annual convening on the west coast.

Tzar and Smayan were not invited.

They had no badge. No booth. No formal introduction arranged through the proper channels that govern such things. What they did have was a text message from the CEO of a publicly traded food distribution company saying he had “maybe a few minutes.” They’d scrambled to find multiple warm intros to the CEO, which led to this very small opening.

“We ‘just happened to be in town’ AKA we flew in after he texted us this,” Smayan explains. “He clearly told us he’s here because he wants us to pitch him.”

So they showed up. Two twenty-six-year-olds who had been best friends since age five, navigating a convention floor. The CEO was at his booth, surrounded by the kind of line that forms when someone controls billions of dollars in annual distribution and everyone wants a piece of the conversation. People had been waiting hours. Nobody was getting more than five minutes.

“We texted him, like, ‘Hey, we also happen to be here. Are you around?’”

The exec responded: “Come say hi.”

What followed was closer to a sparring match than a pitch. The CEO’s opening jab was memorable in its directness: “What do I need all this AI bullshit for? I’ve been in this business for 30 years, I can run it from the back of a napkin.”

There is a moment in most sales conversations where this kind of statement functions as a door closing. The prospect has announced their skepticism—it wouldn’t be the last time. “There would be a second of silence,” Smayan says, “and then one of us would come back with a data point resolving the concern. We just didn’t quit.” Perseverance is key.

“I think the moment where it started to turn,” Smayan observes about the five minute slot that turned into an hour long conversation, “was less about ‘this pitch is amazing’ and more like ‘these guys are special.’ It became about him liking and connecting with us.”

The CEO invited them to come out to the East Coast.

The Week of Six Flights

This part is logistically insane, but it matters because it explains why they won.

In one seven-day stretch, they flew: LA → NorCal → LA → Ohio → LA → (speedrun alumni demo day) → East Coast → LA → SF (speedrun demo day)

Needless to say, their hustle continued. They arrived for the East Coast meeting having slept one hour on a friend’s couch, still processing the red-eye. They expected a casual follow-up—just them and the CEO, continuing the conversation they’d started at the conference.

They walked into a room with the entire C-suite.

“Ten-plus people,” Tzar recalls. “Everyone except the CEO himself, who was the only person who had really gotten us into this room. It’s intimidating. Two of us, ten of them, and they all just come in one after the other, shake your hand, sit down, and announce their title.”

The meeting got off to a rough start. “There was a point early on where someone said, ‘I don’t think you understand what it is we do here,” Tzar says.

Instead of getting defensive or cute, they stuck to the fundamentals:

• paid attention to the energy in the room

• stayed calm

• listened to what people had to say, and reflected their concerns back to them

• kept the conversation anchored in the customer’s workflows

• demoed repeatedly (not once)

• answered objections with specifics

• didn’t bluff

It should have been a disaster, but Tzar and Smayan persisted, consistently demonstrating their product, the value they could offer, and their passion for the space. By the end of a two-hour session, the executives were breaking into small groups and arguing amongst themselves about where to deploy the product first.

“Someone literally yelled across the table: ‘No, you don’t get what this is going to do,’” Smayan recalls. “Then someone else was like, ‘Okay, let’s take it down a notch.’”

After setting a stretch goal of $500,000 in booked revenue, Anchr went on to exceed that benchmark, reflecting the impact of this hard-won enterprise deal.

How you can do the same

There are at least five lessons embedded in this story that you can apply to your own startup.

1. Get on the Plane

The first and most important lesson is physical presence. Tzar and Smayan did not close their largest contract over Zoom. They flew—repeatedly, exhaustingly, at significant personal cost—to stand in rooms with the people who could say yes.

Founder-led sales at the early stage requires being WHERE the decisions happen. Everything from the chit chat in the elevator to the body language you show up with comes into play when clients are deciding whether to spend budget on your product. And it can be harder to say no to someone who flew all the way specifically to see you.

If your deal is six figures and the buyer is on-site, you should be on-site too. The math is simple. The value of a new customer is worth at least the cost of acquiring the customer.

2. Your Greatest Asset is Yourself

The breakthrough at the conference didn’t come from a perfect pitch deck or an irrefutable ROI calculation. It came from two people refusing to accept “no” as a final answer.

“He kept knocking us down, and we kept getting back up,” says Smayan. “I think he respected how relentless we are.”

People buy into founders as much as they buy into products, especially at the early stage. The CEO didn’t invite them to fly out because their AI platform was obviously superior to every alternative. (“It is,” Tzar says.) He invited them because he wanted to see what these two would do next.

3. Overprepare for Your Meetings

Tzar offers perhaps the most precise articulation of what makes early-stage sales work:

“The difference between being successful in go-to-market versus not is: can you turn math into poetry instead of just turning it into prose? If you can pull someone’s heart strings with the way in which you communicate something analytical, that is the moment at which you unlock their cooperation.”

The data matters; how are you going to save your customer time, money or add additional value? But data alone does not move executives. Data needs to be translated into a vision of their business running better. If you aren’t doing hours of research to understand what makes your customer tick before the meeting, what challenges you perceive they have, and so on, then you are wasting your time going to the meeting at all. The 30 minute or 1 hour meeting is a culmination of the hours of research you put into it ahead of time. NEVER walk in unprepared.

4. Gain Access through Multiple Channels

The initial call with the CEO didn’t happen through a single warm introduction. It happened through coordinated persistence.

“We effectively badgered this man through multiple different channels,” Tzar admits. “We had about four unique people reach out to him that were mutual to our network. Some of them reached out more than once. It was a lot. By the end of it, he hated them, and they hated us. But we didn’t stop until we got the job done. You decide when enough is enough.”

Traditional networking advice is to patiently cultivate relationships over time. Founder led sales, particularly in the earliest of stages, doesn’t have the time for that. You need to close deals or your company will be dead in 18 months. It is networking strategically—multiple vectors of intros giving sustained pressure, all with the explicit goal of making it easier to say yes than to keep saying no.

5. Find Your Internal Champion

Once inside a large organization, you need to make other allies.

“The first call we took was with him and his VP of Product,” Smayan explains. “And so this VP of Product has since become our go-to guy. A lot of what helped was that he ended up being in that room with us, and to have someone familiar on the inside that is going to champion you when you face resistance in the broader org—I think that’s huge.”

Understanding exactly who your Champion is vs your Coach is important: a “coach” is someone who likes you but lacks decision-making power. A “champion” is someone who both believes in your product and can influence a decision about your product. It’s also usually in their interest for you to win too.

The Uncomfortable Truth

There is something almost unseemly about this story—the showing up uninvited, the walking past the line, the relentless refusal to accept rejection. It does not fit neatly into narratives about product-market fit or elegant go-to-market strategies.

In early stage sales, the only way through is persistence so unreasonable it becomes its own argument.

This customer did not believe they needed Anchr’s AI platform, and said so explicitly. What they needed, perhaps, was to see two twenty-six-year-olds refuse to believe them. Sometimes that’s enough.

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