Amy Saper of Uncork Capital on how startups should embrace constraints to foster creativity, and her learnings from being at Accel, X, Uber, and Stripe

This episode explores how capital constraints can spark creativity in startups and features Amy Saper's journey and insights from her experiences at leading tech companies and venture capital.

1. Embracing Constraints: Constraints can foster creativity and force a focus on core strengths.
2. Transition Insights: Transitioning from an operator to a VC involves leveraging past entrepreneurial experiences.
3. Strategic Focus: Successful startups often maintain a sharp focus on their differentiators.
4. Resource Management: Effective management of resources is crucial in early stages to navigate capital constraints.
5. Investment Strategies: Venture capital success requires aligning investment strategies with the founder's needs and startup goals.

1: Introduction

Samir Kaji introduces Amy Saper, discussing her background and role at Uncork Capital. Focus on her transition from tech operations to venture capital.

• Samir Kaji: "Welcome Amy, let's discuss your journey from tech operations to venture capital."

2: Embracing Constraints

Discussion on how constraints have driven innovation at companies like Twitter and how these principles apply to startups.

• Amy Saper: "Constraints inspire creativity and focus, which is essential in the startup world."

3: Strategic Focus and Investment

Insights into the importance of maintaining a strategic focus and how Uncork Capital selects and supports startups.

• Amy Saper: "Staying focused on core competencies allows startups to navigate tough market conditions effectively."

4: Venture Capital Dynamics

Exploration of the venture capital landscape, how to support startups, and the dynamics of fund management.

• Amy Saper: "Aligning venture capital support with startup needs is crucial for mutual success."

• Prioritize Core Strengths: Focus on what you do best and avoid spreading resources too thinly.
• Leverage Constraints: Use limitations as an opportunity to innovate and refine your business model.
• Seek Strategic Partners: Align with partners who understand and support your long-term vision.
• Stay Agile: Be ready to pivot strategies based on market feedback and internal assessments.
• Emphasize Learning: Foster a culture of continuous learning and adaptation within your team.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

We are back with Amy Saper, partner at Uncork Capital. Amy shares her journey from Silicon Valley operator at Twitter and Stripe to venture capitalist. She talks about Uncork’s strategy, including its recent $200 million seed fund and $200 million opportunity fund, and how the firm balances growth with specialization.

Investors will find her perspective on non-consensus investing particularly compelling, as she outlines how she evaluates technical teams and market potential. Successful founders attract and develop talent. Finally, she reflects on her move to Uncork and shares her key learnings as an institutional investor.

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About Amy Saper:Amy Saper is a Partner at Uncork Capital, where she invests in seed-stage B2B SaaS, API-first, and fintech companies. Previously, she spent four years as an early-stage partner at Accel where she led seed and Series A investments in companies such as Gamma, Beam, Complete, and Sprinter Health.

Prior to her venture career, she worked at Stripe, Uber, and Twitter launching products, business lines and new markets, in product marketing, product management, business development and international expansion roles.

She received her BS and MBA from Stanford University.

People

Amy Saper, Samir Kaji

Companies

Uncork Capital, Twitter, Uber, Stripe, Accel

Books

None

Guest Name(s):

Amy Saper

Content Warnings:

None

Samir Kaji
Welcome back to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. I'm Samir Kaji and today we welcome Amy Saper, partner at Uncork Capital, where she invests in seed Stage B, two B SaaS and fintech companies. Before joining Uncork in 2023, Amy spent time as an operator at companies like Twitter and Stripe, and also worked at Excel Partners. Today, Uncork has nearly a billion dollars in assets under management and recently closed two sets of funds. Uncork seven, a $200 million fund dedicated to seed stage investing and Uncork plus three, a $200 million opportunity fund for breakout companies.

During a conversation, Amy discussed her transition from being an operator to a vc, the learnings that she transferred over, and her view of why capital constraints foster creativity. This was a fun episode, so lets get right into it. In the fast paced world of startups, every decision counts. And for venture backed startups, choosing the right banking partner can make all the difference. That's why you need to consider Grasshopper bank.

Nationally charted and headquartered in New York City, Grasshopper bank is a client first digital bank built to serve the business and innovation economy, combining the best of banking technology and years of industry expertise to deliver best in class experiences with trusted security and unparalleled support. Join the ranks of forward thinking entrepreneurs who love their digital platform by applying online in as little as five minutes from any device today at www. Dot Grasshopper Dot Bank Grasshopper where banking. Meets innovation Samir Kaji is the CEO and co founder of Allocate. Allocate and venture unlocked are independent of each other.

Any statements or references made by Sameer or his guests regarding third parties investments or securities are solely their views and opinions and are not intended as investment advice or an endorsement of such parties or securities by Samir, his guests, or allocate allocate or its clients may maintain relationships with or investment positions in guests, third parties, or securities mentioned in this podcast. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Amy, it's so great to see you. And thanks for being on today. Thanks for having me.

Samir Kaji
I want to start off with going. Through history because you've had a really. Interesting history at multiple really interesting operating companies, Twitter, stripe, and ultimately you went into VC. And the first question I always ask people that work at these great companies and work within the industry, why make. The change from working at companies to VC?

So maybe you can go through that background. I'm born and raised in Silicon Valley. I grew up around technology and I knew that I wanted to be a part of the startup world in some capacity, and I really fell in love with the entrepreneurial ecosystem. As an undergrad at Stanford, I was able to join a program called the Mayfield Fellows program. I know you've actually had a number of other Mayfield fellows in the podcast.

Amy Saper
Maybe you're familiar. It's a work study program that really exposes you to every aspect of the entrepreneurial ecosystem. And that's how I ended up at Twitter for my Mayfield Fellows internship. Started talking to the team when they were probably 150 or so people. Pre revenue.

First joined as an intern and converted default time. And Twitter had actually never hired a. Non engineering intern before. So I had to write an email to then COO Dick Costello outlining what I saw as the opportunities and how I thought I could contribute as a 21 year old with effectively no work experience. And I'm very grateful that he took.

A chance on me. Still, consider him one of my closest mentors and advisors to this day. Over the course of four years, I got to wear a ton of hats and I think you'll notice some common themes. I wrote a lot of my own job descriptions, so I just kind of. Threw myself at problems and opportunities I saw.

Never paid a ton of attention to. My job title or prior experience. So this was everything from helping build APIs and SDKs for developers, helping small businesses use Twitter, launching new digital commerce products, which a fun fact there is actually how I met my husband. We teamed up on a hack week team. He was also working on Twitter at the time and won hack week and.

Launched new commerce products. I got to oversee the launch of. Twitter's business in 15 emerging markets and. Moved halfway across the world to Dubai and Singapore. And it was just an incredible journey, going from kind of 200 to 4000 employees revenue to a public company, went back to the Bay Area to go to GSB, worked at Uber.

While I was there. In my second year, I met John and Patrick Collison. So the founders of Stripe. I remember walking around the mission in. San Francisco with Patrick and I was just struck by his ability to both predict the future of commerce and sort.

Of where Stripe needed to be based. On where the market was moving and where he saw things going ten years from now and the very short term, which is that Stripe's desktop view of the dashboard was terrible and everyone kept complaining about it. And I thought that combination of the 10,000 foot view and the ten inch. View, if you will, was so rare. And something that I really look for in founders today.

So I had the opportunity to join Stripe in this really unique role where I was the second marketing hire. We had maybe three product managers. I got to work directly for John. Collison and it was sort of a. Hybrid product management product marketing role across Stripe suite of APIs.

So working directly with engineering teams and launching products for marketplaces, subscription businesses and so forth, I learned so much over. The course of three years there that informs the way that I think today. About business models, customer problems, how marketing and product should work together, how to. Think from first principles. And one of my favorite parts of.

My role at Stripe was getting to. Dive into these different business models, whether subscription businesses like Slack marketplaces like Lyft or shopify. And I started angel investing at Stripe as peers from my various networks founded companies and sought out advice. So I realized that venture was a. Way to tie together those two things.

My love of learning about new products and business models and forging those deep relationships with founders and others in the industry, and so had the opportunity to move over to the venture side of things. Having first learned that this was even a job as a Mayfield fellow back at Stanford, joined Excel as an early stage partner. It was just an unbelievable first experience in venture. So I spent four years there and. Got to lead investments in seed and.

Series a companies ranging from AI enabled applications like gamma and logic loop that changed the way people work to embedded fintech companies like Beam that are kind. Of bringing modern fintech tools to legacy. Industries, digital health companies like Sprinter and well theory that changed the way patients receive care today. But I realized over the course of my time there that I'm a startup person of my core. My heart is really in the earliest.

Stages of company building, and from a. Cultural perspective, I just thought that maybe I was better suited for a smaller. Leaner, more entrepreneurial firm environment. And I had heard about uncork through a number of different connections. A founder friend from business school who was now growth stage.

But Uncork had let his seed and. He mentioned Jeff Clavier was the most useful board member he'd ever had. We had a shared investment where Uncork. Led the seed and Excel led the. Series a.

I had another close friend who was on a board with my partner, Andy Laughlin, and I had heard that they were looking for a fifth partner. They reached out and it just seemed like the perfect fit. So I joined five months ago, this past September, and I'm really loving it. I found this balance between a platform that has a real legacy and a strong reputation behind it with this more entrepreneurial approach to firm building that really resonated with me. So here I'm focused on seed stage b, two b apps and API first companies, as well as b, two B Fintech.

Yeah. And it's hard to believe that uncork. Has actually been around for as long as it has. Jeff being one of the first true. Seed stage firms out there.

Samir Kaji
I think it's almost 20 years ago. Now, mainly his own capital at the. Beginning, and of course the franchise has grown. Congrats on the most recent set of funds. I want to unpack a few things that you mentioned.

I do want to talk about the culture of a firm. Search ad juxtaposed a little bit between. Working at a firm and working at a company. I had somebody that you worked with. Before Adam Bain on the podcast recently.

And Adam is very much similar to early days at Twitter, helped grow the revenues from zero to a couple billion dollars was there with Dick, and he actually drew a lot of these insights and thoughts of how he wanted to build a firm with Dick from his interactions with Bill Campbell and how they. Run their firm and what they think about. And one of the things I talked to him about is the similarities, and in some cases, dissimilarities are working at. A startup company thats growing in a startup firm. Now, both of the firms that you.

Joined had been around for a while, of course, Excel being a longtime brand. Firm and uncork being one of the first seed stage firms. But now that youve been in the. Business for four and a half years. On the investing side as an institutional investor, maybe you can juxtapose a little.

Bit between the experiences at stripe and Twitter and what similarities are in running a venture firm. Yeah, no, I think there are a lot of really interesting parallels between culture at various companies and culture and kind. Of operating principles and how you structure. Yourself as a venture firm, a couple of things come to mind. First is everything really comes down to serving your customers and aligning the whole company to do so.

Amy Saper
So in both instances, there might be multiple types of customers, you know, at stripe, perhaps that was startups versus late. Stage companies, or marketplaces versus subscription businesses. At venture firms, that might be your. New founders that you're hoping to form new relationships with, as well as your. Growth stage founders that you've been working.

With for some time, and in addition, your other investors that you work with, your LP's. But really, at the end of the. Day, it comes down to your founders. And your LP's and are you building a great product or service and really delivering on what you have set out to deliver and aligning the goals of the organization with what types of behaviors. Get rewarded, how you choose who to hire.

So I think at the end of the day, that kind of customer orientation, if you will, is fairly shared and it just kind of represents itself in different ways. I think one of the more interesting comparisons, if you will, that I've been. Paying a lot of attention to lately. Is this tension between balancing growth and expansion with specialization and sticking to your. Core watching for scope creep, if you will.

I think in the last couple of years in particular, in the pandemic era, tech boom, a lot of companies and a lot of venture firms really expanded their products, the size of their team, the scope of the types of focus areas or stages that they might invest in. And I think we're starting to see that shift a little bit as companies realize that, hey, resources might be tighter and figuring out how you win in. A competitive environment means sticking to your. True competitive advantage and what you're really, really best at. And so there's no one right way to do that.

But I think the challenge to keep. In mind is making sure that you. Have a strategic rationale behind those reasons to expand your suite of products or your fund size or your focus. And so I do think that that's. An area to pay attention to.

That we'll see movement here, some obvious examples meaning growth stage funds might be retreating from seed. For example, certain funds we've seen kind of realign their sector focus areas, and we're seeing similar things with companies as well, shutting off business lines and trying to stay focused. And I think that's related to the. Overarching theme of leaning into your competitive advantage. So if you're at a startup or a smaller fund, often that's your ability to move faster, create alignment more easily if you're focused on one key product or geo.

So for Unkork, that's north american based seed stage technology companies like startups versus incumbents. I think smaller firms are better able to pivot and evolve their strategy and use speed as our advantage in a deal process. We don't have a complex voting structure. Or the need to wait for a Monday partner meeting to make a decision. A startup doesn't have to wait for the biannual product roadmapping two week long.

Process with 75 decision makers. If they identify an opportunity, they can spin up a team and go tackle that. And then larger multistage firms and larger. Companies have their own advantages. But I think being really cognizant about that and leaning into that is something that I pay a ton of attention to.

I'm a firm believer there's no good cultures or bad cultures. I think Twitter, Uber, and stripe, Excel, uncork, they all had very strong cultures that were very. And I think that I learned there are different things that I've taken away from each of those cultures that I think can be really productive, and conversely, things, elements from all of those cultures that maybe I think could be left behind. And so I think the same thing is true whether you're building a company or a venture firm. I want to extend that analogy because.

Samir Kaji
I really do like the analogy of. Sticking with your core. And certainly when money was easy to come by, and it was easy to. Come by for most of the course. The last few years of the peak period, and really peaking in 2021, people.

Were able to raise money either as. A company or as a firm. And at the company level, you were given a lot of capital because the supply was there. And oftentimes you were forced to either expand quicker than you were ready for. Meaning different geos, different products, when you.

May not have had real product market. Fit, or you were chasing revenue at the expense of unit economics. At the fund level, we saw this. Too many firms were raising bigger and bigger firms funds. Rather, they were doing spvs, they were.

Doing opportunity funds, and the capital was there. And it was really a function of. Adopting almost the business model of your. Funder versus what is right for you. When you think about that aspect of it, how do you know when it.

Is time to expand scope or expand. A product, or when it's too preliminary. Because it's so easy to get caught into it when capital is there. So maybe talk a little bit about the uncorked strategy, because you did recently. Raise the seed stage fund, which is.

200 million, and then you have the growth stage. I'd love to hear how you thought. About it and how the team thought. About this is the right strategy. And although we're expanding maybe the fund size, it's the right thing for us.

To do in staying within our focus. And where we can win consistently. I think, to the point around how did we decide on our fund strategy? And again, I will admit that I joined post fundraise, so I was able. To have conversations through the team.

Amy Saper
And what really struck me about uncorks strategy was it was really this nice balance of a fund size that supported. Our ability to be the lead investors. And the first call, which was really critical to me. It was one of my favorite parts of my role at Excel. There are a number of different ways.

To be an investor, but being the first phone call whenever anything good or bad happens at any time or day of the week is both a responsibility and an opportunity that I think is really exciting. Having the fund size to support the. Larger rounds that are happening at the. Seed stage was critical. We wanted to be able to be.

In the most competitive deals in the best companies. And as our, the average seed might have been five hundred k a decade ago, now it's probably more like three or 5 million. We need to be able to write those bigger checks. We want to be in all the best companies. And so I think our round size reflects that.

And then similarly, it does take companies a long time to go public or. Achieve their ultimate liquidity event. And so we really wanted to be able to maintain our ownership over time. And so having both the $200 million seed fund and $200 million opportunity fund. Enables us to do that.

And that balance was something that really appealed to me. I saw similarities, obviously on a smaller. Scale, with how Excel thought about partnering. With founders at the multistage level. So no matter where you enter, whether it's exceed a b growth or beyond, and being able to stick with founders.

For uncork, we are often the first check, but then we'll stick with the. Company all the way through till their ultimate exit. Yeah, there's a lot there, and some of those things probably deserve a little bit more deeper conversation on the macro side and whether it's the lengthening time companies are staying private and getting to an ultimate exit, rising size of a seed round. And then of course, difficulty of getting downstream financing are all real right now. But right now I'd like to kind of focus on this concept of product market fit within a company.

Samir Kaji
You as an entrepreneur, you know, when you have product market fit, not only are people willing to pay for your product, but they're asking for it. You're starting to see a real scale and you're now reaching a point where you're very clear that there is a viable business model in the world of venture capital. With so many different firms, it takes a while to really understand if you have product market fit with the founders. Are you providing something meaningfully differentiated than other firms that allow you to see and win and build the right type of reputation that allows for long term success? And given the fact that you can now look at your operating background and.

Now you've been in venture, I'm really. Curious to know how you think about product market fit within a venture firm and what really is needed from a delivery standpoint to get true product market fit with the founders you work with. The way that I think about it is it's true that venture is becoming more crowded. I think Seed is incredibly crowded overall. Just like the founders are aligning their product or service with their customers, a VC has to align the ways that we provide value to our founders.

Amy Saper
And I think that for every VC, that is very, very different. And I think that it relates to your ability to both win the competitive. Deals and then also support them moving forward. So for me, when I'm trying to get into those competitive situations, it stems. Typically first from my network.

I'm a very network driven investor, so. Most of the investments I've done to date have been either first or second. Degree connections from my existing networks. I think three of the investments I let it Excel had a co founder from Stripe, for example, and if not, they're likely an intro from a founder or an operator that I've worked with. So I think the way that you get connected to the founder really helps it.

By no means a celebrity VC. I don't tweet a ton trying to blog a little bit more, but I really prefer to keep the spotlight on. The founders I work with and not. Me as an investor. So this feels authentic to who I am.

But it means if we've never worked together, you might not know my value. Add and how I show up for my portfolio. So I try to do this in multiple ways. I think in the earliest days it. Tends to be customer intros, engineer intros, maybe angel investor ideas, and actually got feedback recently from a founder that I.

Ended up not working with but spent. A bunch of time with, who was surprised that I offered three customer intros. And then sent them the same day. Turns out that saying what you're going to do and then delivering it goes a long way in this industry. I also like to show, not tell.

When it comes to value add. So I connect prospective founders with my existing founders, who will underscore how I help tactically and have specific examples of ways that I've done that. They'll say that I'm always on and available, no matter the time of day, the day of week, if I'm on vacation, if a founder needs me, I'm there. I think founders put their entire lives into their companies and their jobs are. So much harder than ours.

So I feel a responsibility to be as available as I can for my founders. I think the last thing that I'll say on product market fit is every vc has their own perspective, their own. Background in terms of what they're looking for. For me, I really gravitate towards technical. Founders that have a unique perspective on.

A market or customer problem. Ideally they've worked directly in that area, who maybe are lighter on the go to market or storytelling side of things, because those are areas that I feel I can really compliment them. And I think one of the benefits. Of leaning into your unique product market. Fit as an investor is it enables you to think outside the box or.

Hunt outside the usual circles. So when I reflect on my ability to identify and source and win the kind of non consensus deals, I think it's often because it's a setup that just really works for my unique background and characteristics. So there's I have my non negotiables around what I'm looking for, which I mentioned, the high levels of technical abilities, their experience in the market. I have to be able to squint. And see a really big market and.

Have alignment with the founder and where things are moving. But I really invest in slope and not y intercept. So I think certain things can be coached, like go to market shops. Storytelling abilities it's essential for founders to learn how to become great storytellers, but. I don't think they need to have those skills.

From day one, John and Patrick did. A bound stripe with the mission to. Increase the GDP of the Internet. I think the first tagline was like the new standard and online payments for developers or something that was not particularly catchy or inspiring. They got better over time.

And I think storytelling, defining your ICP. And excruciating detail, those happen to be. Areas that I love and I have a ton of experience in. So if founders don't have those skills. I'm able to test for a founder's.

Ability to take feedback and iterate. And it really comes down to their. Rate of experimentation, not just with their products, both, all parts of their business. So if I can get comfortable with their slope, I don't care as much about the Y intercept. So for me, product market fit means identifying a founder and a team, and a market and a product that fits my certain areas of focus.

B two B apps API, first companies. B two B Fintech with those sets of characteristics and areas where I think. That my background and skillset can be. Uniquely complementary, I find that when I put myself in those scenarios, I'm both. Better able to win the deal and.

Better able to really help them moving forward. Each founder of course, and each founding. Team is going to have their unique strengths and weaknesses and figuring out where. You can play coach and helping them. Get to that next level is obviously very important.

Samir Kaji
You mentioned some of the non negotiables. You have non negotiables, then you have the negotiables. And in todays world, of course, while. The seed rounds have gone up three. To 5 million, whats also happened is.

The difficulty of raising that next round of capital. That series a the goal posts have. Moved, the bar is higher, theres less capital. One of the things that stood out to me when I was looking at. Your background and thinking back on the.

Twitter days is I think it was biz Stone said something around when you. Have capital constraints or constraints in any. Way, it can launch creativity and were in a capital constrained market. Maybe unpack that a little bit because I know thats something you also hold. Near and dear to your heart in.

Terms of running a fund or helping founders. But how do you see these capital. Constraints actually helping founders in today's world? I'm a firm believer that constraints inspire creativity. As you mentioned, this was one of Bidstone, co founder of Twitter, one of his favorite mantras.

Amy Saper
And at Twitter it stems very literally from the fact that tweets used to. Be sent only via SMS. And back when Twitter was founded, SMS. Could only be 140 characters. 140 character limitations was stemmed from a very real constraint.

But even once tweets started to be. Sent from mobile apps and desktop, and that SMS constraint no longer existed, we found that maintaining that 140 character limit really encouraged people to think more thoughtfully around the message that they were trying to put out. I think that that philosophy can be applied in lots of different ways. And one of the best ways I think startups have to compete is to. Stay laser focused on their core differentiators.

So I'm ruthless about goal setting with my founders, and I'll tie back any big strategic or resource related question to the goals that we've set, particularly in market environments like this. It's really important. I loved Frank Slootman's book amp it up, not have you read that one? I've got to butcher the quote, but something to the effect of narrow the focus, increase the intensity. And I think this is one of.

The best ways a startup can compete. More often than not, I see startups taking on too many responsibilities, hiring too many people, expanding their product suite too quickly, when in fact they can actually. Move faster by staying more focused. And so I think that's one of the unintended upsides of a slightly more challenging economic environment is that it's forcing founders to make these hard trade offs earlier on and really figure out if they have product markets fit to question whether or not they really need to hire as big of a team as they do. And so I think leaning into those constraints, narrowing the focus, increasing the intensity, can be really, really valuable.

And honestly, I think that that's something that I mentioned. The creative constraints inspired by Twitter, I think stripe, at the era that I. Was there, also did this primarily through headcount. So I wish I had. We used to share this graph that would plot stripes, headcount growth relative to.

Revenue compared to our peer set of companies. And stripe was always an order of. Magnitude smaller from a headcount perspective. And so I think that has a couple of implications. It means you have to be very particular about who you choose to interview.

And hire for your company, because not. Everyone can operate well in that type of environment. But for the right type of employee. Who maybe leans a little bit more of general athlete versus specialist, and who likes wearing multiple hats and who likes. Being scrappy, it can be a really incredible opportunity.

So that is something that I think about when I'm talking to my founders and my startups in the early days, is that when you can find that kind of win win scenario with the employees who are self selecting into being in an environment where they're actually excited about the fact that you might be pivoting and evolving and their job description might shift and don't see it as a threat that you can really turn. Your kind of your headcount, your growth into an opportunity. And it makes it a lot easier. To kind of change course down the. Line and avoid the very unfortunate mass.

Layoffs that we've seen in recent years. If you start from the beginning in an environment where you're focused on constraints. The constrained market is fairly new. And actually theres an entire generation of. Both investors and people that have founded companies that never actually operated in this constrained environment.

Samir Kaji
So in many cases, people have had to hit this brick wall, and where. They hired too much, they raised too much capital, maybe the valuation was too high. Theyve had to course correct in a pretty painful way. Now, for companies that are now starting understanding that the market is much more constrained, one of the challenges is going from that Series C to Series A. It's not just how much you have.

To achieve, but you have a shot clock still, and that shot clock might. Be 18 months to 36 months. And you mentioned this aspect of narrowing focus and as a founder, one of the tough things to balance, and we. Face this too, in the company I. Run, is that we see so much opportunity that you want to start to chase all of these different shiny objects because, you know, the revenues there versus.

Doing one thing and doing it really, really well and scaling on that and before moving on to the next. What are you seeing, I guess in terms of what's needed to get to that series A? Because I think a lot of series. A investors still want to see a lot of growth. They want to see traction across multiple things.

What are you advising your founders on? How to balance between staying focused, maybe slower growth, but also understanding there's this. Time period where they have to raise. More capital to be able to continue. As a viable company.

And that sometimes means expanding what you do. You've hit on an interesting distinction, because I do think that one of the ways that startups can compete and win. Is with a faster rate of experimentation. So they can try a lot of things in quick succession. But then I think the key part is to identify and be ruthless with what's working and what's not.

Amy Saper
So it's not that they should just. Try one thing and stay constrained from. Day one, whether or not they're achieving any sort of product market fit, but. Once they've iterated on exactly who their. Ideal customer is and exactly what their.

Sweet spot is, how they can deliver. The most value, that's the point where. You really want to stay constrained and. Pour fuel on the fire in a narrow capacity to give yourself the best. Chance of achieving your goal.

And so I do think that balance is critical. And I think we mentioned unfork shifting. Our fund strategy as seed routes have gotten larger. And I think that that's especially important in today's environment. And so sometimes I will give seed stage founders feedback that they might want to increase the size of their round.

Slightly, such that it buys them a little bit more time to hit those series a milestones. So ideally, you are raising enough for at least two years of Runway, and you want to make sure that you have room for, if things do take. Longer, that you're able to raise your. Series A without needing a bridge. And so I think that's kind of.

One way that I've seen the market start to correct. I do think it's true that the. Bar is shifting at series A. It is harder to raise follow on capital. That being said, I think for great companies, it's absolutely still there.

We've been fortunate that we've had a number of uncorked companies and biotic cell. Companies that have raised series A's in the last couple of months. And so those companies probably are a. Little bit further along in terms of. Their product market fit journey and the.

Revenue numbers, and they would have been. A couple of years ago. But I think going back to this. Point on constraints, staying focused and staying. Lean and preserving your Runway, and just giving yourself more chances to catch lightning in the bottle before you get to the series A is really critical.

If you hire a ton of people really quickly, it's going to be hard to do that. So I actually test for this when I am talking to seed stage founders and I'll have a direct conversation. I think to me, the best tool that I have to figure out, whether I think this founder is one who is going to be operating within constraints and stay nimble, is to ask them to tell me about the round size and why they've decided to raise 4. Million versus 6 million versus 2 million. And to actually work backwards from where.

Does that get you? What milestones do you think you need to achieve to raise a really incredible. Series a now, how do we take that to a more extreme level of detail and go through specifically, who do you think you need to hire? How much are you going to pay those people? Where are you finding those people?

And I learn a lot just from. Hearing about how the founder approaches those things. You know, maybe you don't need four. A'S to hit a million in revenue. I'm a big believer in founder led sales in the beginning, especially, you know.

Till that first million in revenue mark. Through having a conversation with the founder around what resources they need, you can sort of back into how that founder views operating with constraints. You mentioned something that I wanted to double click on. It's this notion that being lean, making sure you're raising enough money in today's. Environment to be able to give yourself.

Samir Kaji
Enough time to experiment and hit the necessary bars to raise the series a from a great group of investors. And when you're investing in some of. These companies and founders, I put the. Founders in maybe two buckets. One is very consensus.

It's a second time founder, it's a third time founder. It's in a market that has a huge tam, very easy to understand. And in those cases, generally speaking, your job is to figure out a way. To convince that founder to allow you to invest. And those rounds tend to be bigger.

And then there's the other group of. Founders, which could be the first time. Founder operating in an industry that's a. Little harder to interrogate and understand. And for those founders may not be able to raise that three to five, maybe thats a two to $3 million round.

Yet they still face the same challenges. In terms of getting to that series a how do you think about your. Model, your own mental model of investing? Because historically in venture where some of. The best returns have happened is when people have been non consensus investing in places where other people havent and founders.

That other people are not generally throwing term sheets at. But it is hard. And so how do you think about the winning versus discovering and doing those non consensus deals? And how do you mitigate the risk. On the ladder bucket?

Amy Saper
I think starting with the ladder bucket in terms of the non consensus deals, I first and foremost rely. I think a lot of it comes down to sourcing. So I rely really heavily on my operating background, which is somewhat non traditional adventure. Today I'm lucky to have been a part of a lot of different organizations. From Stanford, Twitter, Uber, Stripe, I have.

Developed a really deep network of operators. Angel investors and executives at various tech companies who I chat with regularly, where maybe I'm the only seed stage gp that those folks know. So it's actually how I found my most recent investment. A friend of mine leads product at. A growth stage AI company and he told me about this new tool that.

His engineers were absolutely loving. And so before it kind of made. Its way into the radar of the who's who of seed stage venture capital, I was able to have a conversation with the founder, connect the team with a couple of potential early customers, diligence and get to terms. And so I think that network plus speed is definitely something that I use, whether it's a competitive process or not. And then I think going back to how I get conviction on the non consensus ideas, we've talked about some of my non negotiables.

So those have to be met. They have to be a strong technical team with a well informed view on the market or a customer. What's changing? I have to have confidence that the market is big enough to support a billion or $2 billion exit to make. Our fund math really work.

And if those things are there, then I can take risks in other areas. And so to me, being able to figure out the areas that I think the founder needs some work or needs some help on, I really test for their ability to take feedback. I can do this live in a conversation. It will certainly be something that I. Talk about in references, whether on list or off list, is where has this person really grown how have they responded to constructive feedback?

I think that founders have to have tough skin and they're going to be getting lots of feedback. They have to be able to move really quickly. They have to be able to take. In new information and experiment. And so if I can get comfortable with their rate of learning, then I.

Can get comfortable with the areas where. They might seem sort of non consensus or rough around the edges when it comes to taking the leap on that investment. Trey, you talk about the archetypes or the non negotiables. Of course, those non negotiables kind of inform your decision making, whether it's consensus or even a very consensus founder or market. Have your non negotiables changed over time?

They have. One of the non negotiables, one of the biggest takeaways I have for my time at Excel is that a founder has to be an incredible attractor of talent and developer of talent. And that is something that seems sort of empirically obvious. But when you look at what really separates the truly phenomenal founders who become exceptional growth stage CEO's and the ones who I've seen struggle or move more slowly, I think it comes down to their ability to identify, hire, and close that early talent. And I've seen this now sort of.

Across the board in a number of different examples. And typically it's 100 times harder than founders realize to hire really exceptional folks. And so there's a number of different ways that you can test for this. I will often go a layer deeper around their hiring plan, and I don't want to hear we need an engineer. Or even we need a front end engineer.

I want to hear, I worked with. This guy when I was at Snap. And he was the ten X engineer that everyone wanted to work with. I've been stalking him for a year, getting coffee with him every three weeks. And I know that once we close the seed route, if I'm able to, you know, give him this opportunity, he's ready to come on board.

I'm looking for founders that have shown examples of not just having the potential network to find those folks, but understanding. How hard it is and how critical. It is to bring those early hires on board. And so I think that's become a new one of my non negotiables that I've kind of discovered through backing founders that really have that skill and some where it's just been harder to develop. Is that a trait that can be learned, or is that a trait that's innate?

Samir Kaji
Because you have worked at places the twitters and the stripes, where the talent that they were able to acquire was absolutely exceptional and a big part of the success story. It is something that can be learned. Obviously, it's easier to reference if someone has been a manager or been a. Hiring manager, developed teams before, because I. Can think about examples there.

Amy Saper
However, it's different. Being able to attract someone to join. Stripe when you're growing really quickly and a lot of people want to be a part of a rocket ship is very different than joining a risky startup that has no revenue and has a lot to prove. And so I do think that it. Can be learned, and that's something that.

I've been able to kind of suss out through conversations. Actually, one of the founders that I worked with at Excel, who I had previously worked with at Stripe, went the. Staff engineer route at Stripe, so he wasn't managing teams. And so that was an open question. And through the course of our conversations.

Around making this investment, I got to see up close and personal through both. Connecting him with potential engineers from other great companies like Robinhood and so forth. And then talking to those individuals about. How inspired they were to go work for this guy. It gave me enough confidence that he had kind of the innate characteristics that would make him really good at it, even though he had never actually hired.

And managed a team before. And so I think that there are ways that I certainly think it can be learned, but I also think that, honestly, with all of these skills, an aptitude and interest in learning is so tied with success. And this was something that I think Patrick Collison had in spades. He would read like three books a. Week, and famously, you would find him.

Kind of roaming the halls at stripe with his nose in a book. He would bring politicians, CEO's, dignitaries, and his side of a successful conversation was. If he had basically not talked at. All and just asked them questions. It was just so despite having achieved so much success at such a young age, was just so hungry for all.

Of the things that he still had to learn. And so I think whether that's learning how to become a great hiring manager, a great storyteller, a great product builder, I think a proven interest in this kind of insatiable love for learning and a clear talent around experimentation and iterating quickly is more important than prior experience. In any one of those areas. Trey, I want to come back to where we started. I asked you some of the similarities.

Samir Kaji
And maybe dissimilarities of an operating company versus a fundamental. Now, you joined uncork, and as Uncork. Grows over time, you're going to acquire. Talent, you're going to bring new people on and within a venture fund, the people are the intellectual property. At the end of the day, maybe talk to us what made Jeff and Tripp and Andy and the rest of the team so attractive?

You, and how they were able to. Attract talent like yourself. And how did that inform how you're. Going to hire people in the future? What was most striking to me is that prior to meeting and spending time with the uncork team, I had this mental model of venture.

Amy Saper
And remember, Excel is the only venture firm I've ever been a part of. And so in my mind, you could either go raise your own fund, be a solo gp, kind of lose the sort of team aspects that I really loved, and spend half your time or more on the fundraising side of things, but have agency and the ability to move quickly. Or you could be a part of a storied multistage firm where you've had. All the resources and branch that you. Wanted, but maybe things moved a little bit more quickly.

You didn't have as much control over the firm building decisions. And Uncork was this really special balance. To me that I had never seen. Before, where we had this incredibly loyal. LP base, many of whom were shared.

With Excel, which gave me a lot of confidence and a really strong community and network, where if you polled different people who had been a part of the Uncork network, whether they were founders or co investors, just the feedback around the uncorks ability to bring together a community was really paramount. And that was something that really stood out to me. I'm a very, you know, I'm a competitive person, but I'm a collaborative person. And I think it's hard to find a combination where when we're trying to compete and win a seed deal, everyone kind of shares that same competitive drive. But we don't see venture as a zero sum game, and we appreciate and.

Understand that we actually need to build those relationships with angel investors, pre seed. Funds, growth stage investors. And that just really appealed to me. And kind of spoke to my strengths around the network, really driving so much of my career. And so I think that was certainly part of it.

Obviously, the results kind of speak for themselves. I wanted to join a top performing seed fund, uncorked consistently. When I would talk to my friends, that sequoia or Andreessen or even Excel was always one of the names that they would track very closely. So I think those things really appealed to me. And then I think more than anything, it's a collection.

So where general is fun, but everyone has their areas of focus, and it's collaborative in a way that I found really unique, where a lot of venture firms can kind of feel like lone wolf games. And at the end of the day, you're, you know, you're the board member. You'Re the investor, you're winning the deal. But I've now seen this up close. And personal in the last five months.

And I've been able to both help out with companies where the investment obviously predated me and get on the phone with founders and help them walk through authority issues. I've had a lot of founders ask for help on getting access to new beta products or people at stripe. And then similarly, when I'm trying to. Win a deal, my partners have gone. Above and beyond to connect their founders.

With the prospective founder and share what. The experience is like as an uncork. Founder, to connect the founders with prospective customers that are from their own personal networks. And so I think that sort of collaborative approach to investing really appealed to me. And I think that there's something really special about being a generalist fund that's made up of individuals with particular areas of focus, expertise.

And so we have a mix of former founders, career investors, company builders like me, and I think it enables us. To provide just a really rich and multifaceted experience, experience for our founders. And so that was something that kind of pushed me over the edge in terms of joining uncork. Now it's been half a decade as. An institutional investor, longer when you count your angel track record in terms of.

Samir Kaji
Investing in companies, what's the one thing. That you know now that you wish you knew when you started investing? Throw the rulebook out the window and. Question the status quo. You've probably picked up on the fact that I have a sort of healthy impatience and a discomfort with stasis.

Amy Saper
And I think it's one of the reasons I get along so well with founders. And I didn't recognize it as such early on. But I'm not satisfied with an answer like, well, this is the way it's always been done. And I think when I look at. The founders that I respect the most.

They share that kind of disregard for the status quo, you know, in a healthy, polite way. I think John and Patrick would refer to this as thinking from first principles. And I think it's part of why they've been so successful with stripe, not. In spite of the fact that they. Didn'T come from payments, but actually because of it.

So I think, you know, chasing the hard problems and asking the tough questions early on and not being afraid to try a new approach can really lead to great outcomes. And I think kind of feeling comfortable with the with the discomfort and understanding that you might not have had experience in a given area. But that doesn't mean that you can't potentially see around corners and identify what could be a really great new business opportunity. SpaceX is a great example of it. It's not like Elon Musk had a.

Samir Kaji
Long history in space as a business, but he realized that there was a. Better way to do it. And I would agree. In fact, my biggest pet peeve is. When I do hear people say, oh.

Well, that's the way we used to do it. Well, we're not building for something in. History, we're building for the future. So great insight, Amy. This was a lot of fun.

Congrats again on joining uncork. It's a great group of people and really excited to see you in the firm grow. Also, thanks so much for having me. Samir, thanks so much for listening to another episode of Venture Unlocked. We really hope you enjoyed it.

To learn more about Amy, me or uncourt, be sure to go to the Ventureunlock substack at Ventureunlock dot substack.com, where you'll find detailed notes of the show and a listing of past episodes. You'll also find us on Apple or Spotify, where you can subscribe to get all of the latest shows as soon as they're released.