entrepreneurship | springload

By Eric Picard

I’ve been getting a lot of outreach lately. Brilliant people, world-class engineers and research scientists, some of the smartest humans I’ve ever met, are reaching out about AI startups they want to build. Most of these folks have made real money in their careers. They’re self-funding the early work. And almost all of them are about to get a very rude awakening.

These folks are coming to me because they know I’ve done four startups, and that I’ve raised money before. Bluestreak, my first startup, raised $28MM between 1997 and 2001. I will tell you for certain that the seed funding was the hardest part. We raised $150,000 from local angels, and then $1.3MM from some professional angels. Then a Series A, Series B, and Series C. Every one of those raises was incredibly hard. Rare Crowds, my second startup, raised $750K and it was harder than any of the fundraising we did for Bluestreak.

My engineering and scientist friends know that building the technology is hard. They’re right. But they assume that’s the hard mountain to climb. It isn’t. Building the technology is the mountain you already know how to climb. Raising the money is a different mountain entirely, and brilliance in engineering and science does not transfer natively to climbing that mountain, it’s a whole new skillset to learn.

It isn’t about talent or ability. These are people who have never failed at anything in their professional lives. They excelled academically, landed elite research roles or senior engineering positions, built things other people couldn’t. That track record makes it very hard to see what’s coming. Startups are harder than anything they’ve done before, and fundraising is a completely different skillset than building technology. If I had to bet on the one thing that will most surprise them, it’s that.

Raising money is selling a piece of your company

Fundraising is selling a stake in your company to a stranger who has no reason to trust you, based on a pitch about an unproven future. You are asking them to take a risk, and your job is to mitigate that risk in their mind with three things: a genuinely innovative idea, a technology problem that is hard enough to defend (what investors call a moat), and evidence that your team is the one that will win.

That last one matters more than most first-time founders expect. Investors invest in teams as much as they invest in ideas. Most companies pivot multiple times. The idea you’re pitching today may not be the business you’re running in three years. Experienced investors know this, and they’re betting on whether you and your team can navigate the chaos of a startup, not just whether the technology works as advertised. And it isn’t just one member of the team, they’re looking for a strong team that works well together.

So you’re not just pitching a product. You’re selling yourself, your team, your judgment, and your ability to execute under conditions that are nothing like the well-resourced environments most technical founders have thrived in. Brilliant engineers trying to raise money are not expert at fundraising until they have a lot of experience doing it. And most of them are starting from zero.

This also goes for product managers reading this. You’re a hybrid, part business and part technology, and it’s tempting to assume that gives you an edge in the room. Maybe. Maybe not. Don’t walk in overconfident. I’ve seen product people get just as humbled as their engineering co-founders, because pitching investors is its own craft, and it doesn’t care about your functional background. It’s much closer to sales than engineering.

The numbers, and why they should reset your expectations

This has been studied carefully, and the findings are sobering.

DocSend, working with Harvard Business School, analyzed hundreds of startups across multiple years. The headline finding for a successful seed round: founders contacted an average of 58 investors and held around 30 to 40 meetings before closing, over roughly 12.5 weeks. By 2023, the average was 66 investors contacted with about 38 meetings set. Series A is different. By then your track record filters the funnel, and founders contacted an average of 26 investors rather than 58.

Nathan Beckord of Foundersuite, who has run many raises, puts the conversion rate plainly: he pitched more than 200 investors and landed one seed fund and 10 angels, a roughly 5% conversion rate, and calls that “pretty common.” The 2026 benchmarks from Founder Institute tell founders to prepare to pitch 100 to 200 investors.

Here is the actual funnel, using the data as reported:

You contact roughly 58 to 66 investors to run a seed round.
About half convert to meetings, roughly 30 to 38.
Roughly 3 to 5 write a check, around 5% of the people you contacted.

Two ratios to internalize: about half your outreach should turn into meetings, and about 1 in 10 of those meetings turns into money.

The founder who takes 8 or 10 meetings and concludes the market is closed has not run the funnel. They haven’t finished yet.

Meetings matter more than outreach volume

The insight buried in the DocSend data that changes how you should think about this: it’s not the number of investors you contact that predicts success. It’s the number of meetings you get.

In one cohort, founders who didn’t get funded actually contacted slightly more investors than those who did, 77 versus 70, but landed far fewer meetings, averaging just 15. The funded founders got roughly twice as many meetings from roughly the same outreach.

This means meetings are the signal to optimize for, and not just because more meetings mathematically means more chances at a check. Each meeting is a rep. You get feedback, you adjust the pitch, you sharpen the story. Later pitches with a more refined narrative, and with more evidence of traction as you build, are meaningfully more likely to succeed than your first few. The pitch you give in month one is not the pitch you give in month three, and it shouldn’t be.

Not all ideas are fundable as standalone companies. Some things that are technically impressive are better as a feature inside a large platform, or as a services business, and experienced investors recognize that immediately. If you’re pitching a fundable idea and getting meetings but not money, your pitch is the problem. If you can’t even get the meetings, the targeting or the narrative is the problem. Either way, the fix is more reps and more feedback, not just more outreach.

Know who you’re pitching

This is where a lot of first-time founders waste months and burn their best opportunities.

Venture capital firms, the branded ones you’ve heard of, primarily invest in later seed rounds and Series A, and some focus on later stage (Series B and C) rounds. If you’re connected, some will take your meeting, especially if the technology is interesting. But the most likely outcome is a genuine, friendly conversation that ends with, “This is exciting, come back when you’re further along.” That is not a rejection. That is an investor telling you what milestone will get them in. Keep the relationship warm. It has real long-term value. But it does not put money in the bank this quarter.

For pre-seed and early seed funding, the capital you need to build something worth pitching to a VC, your target market is angel investors. Specifically angels who invest at your stage and in your sector. Research them. Find out what they’ve funded, what stage they enter at, what check sizes they write. This is sales 101 applied to fundraising: know your customer before you walk in the door.

One other misunderstanding that’s worth calling out: If they didn’t say yes, they really said no. A polite, super interested conversation isn’t a yes. A promise to bring your idea to their next review meeting with their partners is a win. But it’s not a yes, and it relies on that partner being able to articulate your pitch (note: your leave-behind materials are important.) So individual investors are easier, they can make the decision on their own without convincing anyone else. You’re better off getting a fast “no” instead of a slow “no.” Don’t be discouraged by the fast “no”, be happy it was fast. Ask for clarity on why they said “no”, and hope to glean input that can help hone your pitch for the next investor.

The problem of overfitting on success stories

Exceptional people are more susceptible to this trap than most, because their own lives keep providing the evidence.

Jim Carrey famously told graduates to take risks and follow their dreams. He’s living proof that it worked. What he can’t tell you about is the thousands of genuinely talented comedians and actors who took the same risks, worked just as hard, and didn’t make it, because we’ve never heard of them. Talent matters. Jim Carrey is exceptionally talented. He was also very lucky, and luck doesn’t scale to everyone who deserves it.

Here’s the piece that gets underappreciated: talented actors trying to get cast in roles are not expert at auditioning until they’ve done it hundreds of times. The audition is a separate skill from the craft. Talented engineers trying to raise money are not expert at fundraising until they have a lot of experience doing it. Experience tips the scale. Pitch a lot.

The standout AI startup raises you’re reading about, $20M at a $200M valuation pre-revenue, are the Jim Carrey story. They are not the base rate. They are the outcomes you read about because the others didn’t make the news.

This matters for how you plan. Your talent is real. Your odds are better than average because of it. They are still hard.

Product-market fit is not a buzzword

You’ll hear “product-market fit” constantly. There’s a reason. Tuning what you’re building to what the market actually wants, or can be convinced it wants, is one of the hardest and most time-consuming problems in building a company. Most early startups are wrong about this at least once before they figure it out. Most are wrong more than once. Success isn’t about betting once, it’s about betting, learning, and betting smarter the next time.

Investors who get in ahead of product-market fit are betting almost entirely on the team. If you can show early evidence of fit, even a handful of paying customers, even a waiting list with real signal, you dramatically increase your chances. Every proof point you can put in front of an investor reduces the risk they’re taking on, and risk reduction is the whole job of the pitch.

It takes a team with all the right skills

I want to make a case for something that brilliant technical founders are often the most resistant to hearing.

The best salespeople and business people are not less intelligent than engineers and scientists. They’re differently intelligent. Building relationships, reading a room, navigating objections, understanding what someone needs to hear before they’ll commit, these require a kind of emotional intelligence that is just as rare and just as valuable as the ability to solve hard technical problems. High EQ is a real capability, and in a fundraise it may matter more than high IQ. The two are not in competition. They’re complements.

The great ones are comfortable with rejection in a way that most technical people aren’t wired to be. They think in pipeline. They treat objection-handling as a craft. They genuinely enjoy the human dynamics of closing a deal. Finding someone great at this is as hard as finding a great engineer. They’re just hard in different ways.

Building a founding team is not a hiring problem. It’s the most important set of relationships your company will ever have. But if your founding team is all technical depth and no sales or business instinct, you are going into the hardest sales process of your life, raising money, without anyone on the team who has ever done it before.

Think hard about that before you start pitching.

Let’s talk about the roles and the real job description from the lens of a startup. I’m going to use C-level titles, but you can extrapolate. And remember, a 5 person company with 5 C-level titles isn’t necessarily a good idea or a bad idea.

The real job descriptions

CEO: Your job is to make sure the company has enough money to survive. Period. You’re on the hook to make payroll. To ensure that the AWS or GCP, Anthropic or OpenAI, BigQuery or Snowflake bills are paid. Your job is to make sure the company lives through the startup experience. This means you own the investor relationship, and you need to actually own it. It’s one of your many full-time jobs. Even if you’re a technical CEO, or if you’re a product CEO – your primary job is making sure the company survives to continue – which means you own the investor relationships.

CTO: Build the thing. Innovate enough to differentiate. But build the thing. Fast. Take the right shortcuts, you’re not at a F500 company. Amazon, Microsoft, Google – they all have early-days stories about technical risks and shortcuts they took. Often laughed about, as in, “I can’t believe we had $5M in sales running on a server under Jim’s desk. Remember the time the cleaning person unplugged it?” Make sure your shortcuts are the right shortcuts, not the wrong ones. Make sure they’re survivable.

Chief Product Officer: Figure out the thing that will find product-market fit. Talk to the market. Develop a hypothesis. Test and retest it. Apply learnings. Convince the CTO to make the changes. Package the idea so it can be sold. Startups overfit against invention and building, and underfit against “Go-to-Market.” Don’t forget that great products fail all the time, and weaker products win all the time because they were brought to market better. Listen to your sales inputs on how the pitch was received, and tune both the product and the pitch!

Chief Client Officer: Make any customers happy at almost any cost. Winning a customer is super hard. Keeping that customer happy is also super hard. Keep them happy, churn is not something an early stage startup can weather as easily as a late stage startup. Make up for product shortcomings with human effort, but make sure it’s not permanent.

CRO: Build a pipeline, and convert. Do it with investors. Do it with customers. Hone the GTM pitch on both decks, learn and adapt. But close at all costs. Revenue does two things: It funds the company to offset burn rate, and it proves to investors that you’re on a path to product-market fit and ultimately to success. Be methodical, analytical, and get to 10% week-over-week and month-over month success metrics (or better!)

Why the CRO matters more than technical founders think: The right founding team for most successful technical startups includes someone who lives for the close, isn’t wounded by the no, and wakes up thinking about how to move people from interested to committed. That person needs the engineer as much as the engineer needs them. The technology without the ability to sell it is a project. The ability to sell without something genuinely hard and defensible behind it is a dead end. Together, you have a company.

Fundraising is a grind. It takes months, hundreds of contacts, dozens of meetings, and more patience than most people who’ve never struggled professionally have had to develop. The technology problem is hard. The fundraising problem is harder in a completely different way. Go in knowing that, prepare for it like the discipline it is, and find the people around you who are as talented at selling as you are at building.

You’re going to need each other.

By Eric Picard

In my career as a Chief Product Officer, I’ve had the opportunity to witness firsthand the evolution of product management roles in both small and large companies. This journey has given me a unique perspective on the challenges and opportunities that product managers face as they navigate these different environments. Today, I want to share some insights on how product management scales from small organizations to larger ones and a little story I like to call “The Parable of the Rocks.”

“HEY! Give me back my rocks!”

In smaller organizations, product managers are like Swiss Army knives. They juggle an array of roles, from product marketing to technical product management. This requires a versatile skill set and the ability to adapt quickly to shifting demands. In these environments, the scope of each role is broad, and resources are often limited. The challenge lies in effectively balancing these diverse responsibilities. The ability to switch contexts seamlessly and maintain organization is not just a helpful trait; it becomes a superpower.

For instance, a product manager in a small company might start their day aligning the product roadmap with the engineering team, spend the afternoon crafting go-to-market strategies, and end the day troubleshooting technical issues. They are the glue that holds disparate functions together, ensuring that the product not only meets market needs but also stays on track with the company’s overarching goals.This breadth of responsibility fosters a deep understanding of the product and its ecosystem. However, it also means that product managers in smaller companies often feel like they are carrying the weight of the world—or at least the product—on their shoulders. It’s a fast-paced and demanding role, but it also provides an unparalleled learning experience.

There comes a time in every company or team when the work becomes too much for one person, and that’s where things get very interesting. Eventually the work gets split across multiple product managers. Sometimes that individual contributor becomes a manager and has to divvy out their work. Sometimes a product leader is hired into the company as well. And as organizations grow, the product management role becomes more specialized, breaking into a variety of focused positions that allow for deeper expertise and efficiency.

Product Marketers focus on the Go-to-Market strategy, developing value propositions, creating sales materials, and assisting marketing and sales teams in targeting prospects. They decide whether to roll out by geography, market segment, or industry vertical, and prioritize efforts accordingly.
Product Strategists spend their time analyzing market opportunities, engaging with analysts and customers, crafting Market Requirements Documents, and conducting competitive analysis. Their role is to understand where the product fits in the market and how it can best meet customer needs.
Product Analysts or Product Operations Specialists ensure that products are properly instrumented for capturing user activity, enabling path analysis and financial performance evaluation. They provide invaluable insights into how the product is used and where improvements can be made.
Product Designers are responsible for the product’s look and feel, focusing on usability and user feedback. They conduct both qualitative and quantitative analyses, ensuring that the user interface is intuitive and effective.
Technical Project Managers coordinate the various teams and deliverables, ensuring that deadlines are met and resources are allocated efficiently. They play a critical role in keeping projects on track.

This specialization allows Technical Product Managers to concentrate on a more focused yet still pivotal role. They “own” the product, defining what will be built, prioritizing features on the roadmap, and writing the specifications that engineers use to develop the product. They still need to talk to customers, and they still need to stay on top of the market, but now they have help from partners. The Product Manager role now requires even more synthesizing input from various stakeholders, convincing the organization that their vision is the best way to tackle business challenges. They need a strong ego to hold firm opinions backed by data, yet remain open to ideas coming from anywhere. This all sounds wonderful, but the organizational transition and the personal transition that these previous superstar unicorns have to go through can be daunting.

This brings me to a story I often share when discussing this transition, which I call “The Parable of the Rocks.” Imagine being a product manager in a small team. Your day is spent picking up rocks—tasks, feature areas, responsibilities, and challenges—and putting them in your backpack. As the product develops and matures, you accumulate more and more rocks, and your backpack grows heavier. Eventually, it’s breaking your back. You’re walking hunched over, struggling to move forward, your chin is almost scraping the ground.

Finally, the company recognizes the need for help and hires a new product manager or even a leader for the PM organization, or splits the responsibilities out into some of these specializations mentioned above. This new person walks in, sees you bent double under the weight of all those rocks, and says, “Oh my god, let’s get some of that weight off.” They take some rocks out of your backpack, and either put them in their own backpack, or they hand them off to other PMs or teams. If that person is a new product leader, they might decide, we shouldn’t be doing some of these things, and they might throw those rocks back on the ground.

At first, the product manager feels relief. They stand up straight, stretch, crack their back, and take a few steps forward. But then they notice those rocks on the ground, or see others carrying them, and doing things with them differently than they’d have done, and they say, “Hey, those are my rocks! Give me back my rocks!” This parable illustrates a common pitfall in transitioning from small to large teams. It’s natural to feel a sense of ownership over tasks you’ve been managing, but it’s critical to embrace the shift.

Letting go of certain responsibilities allows you to focus on strategic priorities and leverage the strengths of a larger team. It can be very hard to let go, because the new person who owns that rock might see it very differently, might change the very nature of a feature and how it solves the customer problem, or might deprioritize that feature altogether. The transition from small to large companies can be a transformative experience for product managers. It requires a willingness to adapt and a readiness to embrace new challenges and opportunities. Here are some strategies to navigate this transition successfully:

Develop a Growth Mindset: Be open to learning and adapting to new ways of working. Embrace the opportunity to deepen your expertise in specific areas and collaborate with specialized teams.
Cultivate Strong Communication Skills: In larger organizations, the ability to effectively communicate your vision and align cross-functional teams is paramount. Become a great data-driven storyteller. Inspire your teammates, inspire your customers. Foster relationships with stakeholders and build a network of allies.
Focus on Strategic Impact: Learn to balance bot the day-to-day tasks with long-term strategic goals. Leverage the resources available to you in larger organizations to drive meaningful impact. Don’t feel like you need to own all the rocks.
Let Go of the Rocks: Recognize the value in delegating responsibilities and sharing the load with your team. Trust in the capabilities of others and focus on the bigger picture.
Embrace Change: Change is inevitable in the transition from small to large companies. Embrace it as an opportunity for growth and innovation.

Scaling product management from small to large organizations involves a shift in mindset and approach. It’s a journey that offers both challenges and rewards, and one that can ultimately lead to greater strategic impact and career fulfillment. Embrace the shift, learn to love to give your rocks away, but ensure the new people have all the context they need to value them appropriately. Learn to tell great, inspirational, fact-based and data-driven stories. It’s only by convincing others that what you believe should be done or built that you’ll win – both as a company and you personally as part of your career development.

springload

A Product Strategy Consultancy focusing on Ad Technology and Online Media consultancy

Tag Archives: entrepreneurship

Tech Startups are hard: Fundraising is the hardest part