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How to pitch me: 15 investors talk about what they’re looking for in August 2023

'I suggest reaching out right before Labor Day to set up a meeting in September'

Walter Thompson @yourprotagonist / 8 months

Summer 2023 has been the hottest one on record since 1880, but while early-stage founders were sweating over the order of the slides in their pitch decks, many of the investors they hoped to connect with were playing pickleball in Jackson Hole or relaxing poolside with cocktails in Palm Springs.

August is one of the slowest months in venture capital, which is why now is such a good time for fundraising founders to ramp up their outreach efforts.

“People tend to be out of the office longer than usual this time of year,” says Kittu Kolluri, founder and managing director of Neotribe Ventures. “I suggest reaching out right before Labor Day to set up a meeting in September or wait and start your outreach altogether next month.”

August is one of the slowest months in venture capital, which is why now is such a good time for fundraising founders to ramp up their outreach.

With that in mind, here’s the latest edition of “How to Pitch Me,” a recurring column that gathers tips, insights and strategies from early-stage investors who are interested in making deals.

There’s a lot of actionable advice in here: If you’re wondering how much previous experience with AI investors are looking for, which questions to ask once you’re in the room, or just need a level set on CEO salaries, please read. These responses have been edited for space and clarity.

Thanks very much to everyone who participated:

Christine Hsieh, venture partner, Third Culture Capital

What kinds of investment opportunities are you looking for right now?

We are looking for teams of uniquely qualified founders who, through their diverse experiences, cultures, identities, and training have a distinct advantage in building world-changing healthcare companies. Our sector and stage focus include digital health and techbio companies who are at seed or pre-seed stage.

How do you prefer to be approached: a cold email, a warm intro, or another method?

As an effort to break down barriers that have historically excluded far too many entrepreneurs from venture investment, we encourage entrepreneurs to reach out to us via our online submission form, without requiring a warm introduction.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

In healthcare, you need domain expertise on the team no matter how strong you are at AI. The complexities of the stakeholders, processes, and regulations involved are too high for “normal tech disruption” to work as you might see in sectors that aren’t as conservative.

For care-delivery startups, we like to see clinicians either as part of the founding team or with a committed role as an advisor.

In August 2023, what are some of the top questions founders need to ask investors?

  • How can you help me with our gaps and growth goals?
  • What are your expectations on timeline to profitability?
  • What’s your position on follow-on funding?

What’s a traditional pitch tactic that no longer works but is still a common practice?

Less a pitch tactic, perhaps a business strategy: asking for too much money with little to no traction. The bar is higher now.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

We are open to reviewing any supporting documents as long as they tell your story and the business’ potential well.

Tell us about the best pitch you’ve received recently: At what point did you realize you were going to invest?

A recent great pitch we saw came from a founder who was very obviously deeply knowledgeable about the problem they were solving, and the thinking behind a few different strategies they’d possibly take along with their trade-offs.

We realized we wanted to invest when we saw the perfect combination of a founder we were highly confident in, building in a white space with lots of room to grow, and with solid paths to market that they could pivot between if needed.

What are you reading/watching/listening to right now?

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Marta Cruz, co-founder and managing partner, NXTP Ventures

What kinds of investment opportunities are you looking for right now?

We exclusively invest in B2B companies in Latin America. We predominantly invest in B2B companies in pre-seed stage and seed-stage companies, usually becoming the first institutional check into the business. We also invest at the Series A stage, although a little less frequently. Our typical check size for seed rounds ranges from $500,000 to $3 million USD and we like to lead or co-lead rounds.

As a sector-specific and thesis-driven fund, we concentrate on cloud and SaaS, e-commerce enablers, fintech, B2B marketplaces, and AI and data-driven businesses.

How do you prefer to be approached: a cold email, a warm intro, or another method?

While we are open to cold emails, warm introductions through our network generally stand out more. It demonstrates that the founder has done their homework and has already begun networking in the industry.

If you’re comfortable doing so, please share your contact info.

You can get in touch with me on Twitter @marta_cruz and for more formal interactions, our website provides a point of contact.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

For nontechnical founders or those not primarily in the AI space, we emphasize deep domain expertise and the ability to attract and manage a solid technical team, where the ideal combined experience could include machine learning experts, data scientists, software engineers, ethics, and policy specialists.

We must keep in mind that AI is a collaborative effort and that diversity of knowledge often leads to more successful and innovative results. Therefore, a competent AI team must demonstrate leadership skills, a comprehensive understanding of customer needs, and a clear vision, just like in all teams of entrepreneurs, regardless of the technology they use.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

We are open to reviewing both pitch memos and completed decks. The key is to clearly and succinctly communicate the business’s value proposition, market opportunity, roadmap for growth, and, of course, the founder team information and what the startup is looking for.

What are you reading/watching/listening to right now?

Two books at the same time:

Adam Struck, founder and managing partner, Struck Capital

What kinds of investment opportunities are you looking for in August 2023?

We have spent a significant amount of time this year understanding where startups can capture the most value and have come up with a few areas where we are excited to invest, most notably in verticalized applications of generative AI and in middleware (tooling and infrastructure) that supports the development of new AI applications.

These two investment theses work in concert with one another, as any company that ingests proprietary data from its verticalized application will need tooling to orchestrate and optimize this data so it can continue to create specialized workflows for its end users. We are looking forward to seeing this new trend continue to evolve.

How do you prefer to be approached: a cold email, a warm intro, or another method?

We want to speak to the best and brightest founders, regardless of whether the introduction came from someone within our network or from cold outreach. With that being said, a warm introduction can help us cut through some of the noise, as we receive dozens of pitches each day.

If you’re comfortable doing so, please share your contact info.

info@struckcapital.com

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

While a founder with deep domain expertise through decades of working in AI and ML is certainly compelling, we don’t want to exclude ourselves from working with founders earlier in their professional journey.

With the latter founder archetype, we would look to understand their genuine interest and depth of understanding of the technical advancements in the space.

Generally speaking, how much salary should the founder of a pre-revenue startup in a Tier 1 city pay themselves?

We typically categorize companies by funding raised, rather than by whether they are generating revenue or not, as some businesses are inherently more capital intensive than others. For the SaaS businesses that we primarily invest in, this means they will have likely raised under $2 million. We like being as data-driven as possible and will use Pave to benchmark salary recommendations.

In August 2023, what are some of the top questions founders need to ask investors?

You are increasingly starting to see more startups not able to reach their next set of milestones as quickly as they hoped, and consequently not able to raise a next round of financing. It’s important for founders to understand how VCs have handled these interactions previously.

It’s easy for a VC to be highly supportive and go the extra mile for their fastest-growing companies in their portfolio; however, what’s more indicative of their future behavior is how they support companies experiencing more hardship. Look to speak with a founder in their portfolio who “failed,” or ask if the VC has a strategy around continued financial support in between funding rounds.

What’s a traditional pitch tactic that no longer works but is still a common practice?

We still encounter pitches that revolve around founders preferring to present their entire pitch deck and take questions at the end. We much prefer an engaging back-and-forth discussion around specific questions we are interested in learning more about.

A discussion results in much deeper insights from a founder, which can be extremely helpful in deciding if we want to dig into further diligence. For founders, a discussion-based approach can be more beneficial too, as it lets them understand exactly what investors want to learn more about in a more thoughtful manner. These insights can be helpful as the founder goes through their fundraising process, as they can tailor their pitches to inoculate against specific risks.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

Typically, we prefer a completed deck, as this lets us be as prepared as possible for an introductory conversation with a founding team.

Tell us about the best pitch you’ve received recently: At what point in their presentation did you realize you were going to invest?

We prefer to run diligence processes that stretch across a multitude of conversations, with each discussion compounding upon one another, as we and the founding team become increasingly excited about partnering.

It’s difficult to pinpoint an exact moment, but we had the privilege of hosting the founding team of our most recent investment at our office in Santa Monica. The team really impressed us with their large vision and execution to date as well as the mission-driven ethos of their product. We are always excited to back revolutionary founders building for the right reasons.

What are you reading/watching/listening to?

I’m currently reading “Four Thousand Weeks: Time Management for Mortals” by Oliver Burkeman and finished watching “The Diplomat” [on Netflix]. I recommend both!

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Adam Nash, angel investor, CEO and co-founder, Daffy

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I have made investments in founders who used both of these approaches, although I find that there is no good substitute for a founder walking me through the narrative of their company backed by a completed deck. For the initial request for a meeting, however, I’m very happy to receive either a well-written memo or a deck.

In August 2023, what are some of the top questions founders need to ask investors?

Founders are well advised to be cautious when including angel investors who are new to investing. Most seasoned angel investors know what their model is and realize that most companies do not return capital. It can be incredibly distracting and difficult to deal with small investors who have unrealistic demands on a startup, especially when the company hits the inevitable challenges with product, distribution, and financing.

For institutional investors, it is critical to understand what the model for the firm (and the fund) is, as well as how those investors behave as board members and partners in building the business. Investors come with many different backgrounds, styles, and areas of expertise.

Raising capital at early stages is a hiring decision, not a financing decision. Trust is critical. A bad investor is difficult to deal with, but a bad institutional investor can kill the company.

What kind of investment opportunities are you looking for in August 2023?

In fintech, I’m looking for three things:

  1. Product-founder fit: I need to believe that the founders have a genuine passion for the problem they are solving, not just a path to make profits. Most of the worst stories in financial services come from ambitious founders chasing profits instead of focusing on their customers.
  2. Real value: I need to see financial products that will generate economic value, both individually and at scale. Too many fintech ideas continue to lack academic and intellectual rigor, and those chickens come home to roost.
  3. Distribution strategy: I need to understand what customer segment this product is designed for and how to reach them in sufficient numbers to build a venture-scale business.

How do you prefer to be approached by a founder with their initial pitch: a cold email, a warm intro or another method?

A warm intro is always best because it kills two birds with one stone: You get the intro to the founder and company and some form of endorsement and referral. Cold email can work, but only if the founder has put genuine work into the approach and understands who I am as an investor.

What’s one traditional fundraising tactic that founders should remove from their toolkit — something that no longer works but is still a common practice?

The idea of pitching hundreds of investors in some sort of statistical approach is a mistake. A startup is not like a company going public — you are not just orchestrating a roadshow and bidding. Your early investors are critically important to the success of your company: The best will not only give you advice but also open doors for you for financing and go-to-market. Bad investors can be a distraction to execution and torpedo future financing rounds.

A lot of founders are learning the hard way in this market, and there is more pain to come. Think of your early fundraising as a hiring decision, not just a financing process.

Tell us about the best pitch you’ve received recently. When during their presentation did you realize you were going to invest?

In March, I made a small investment in Owner.com, sort of a Squarespace for local restaurants. No deck, just a long-read document. But it was only when I met the founder and we talked through the issues around distribution and delivery that I realized that he had already spent significant time on the issues and had turned them into strengths for his platform.

When I ask questions of a founder, like most investors, I believe they are well-grounded, intelligent questions. This is the opportunity that many founders miss. Embracing the question and the strategic issues underneath it is a chance to show investors that not only do you understand the market theoretically, but [you also] demonstrate that you’ve given prior thought to those issues and have real, practical ideas on how to address them. Give an investor new insight, they will lean in. This is how Dylan got me to invest in Figma back in 2013!

What are you reading/watching/listening to right now?

Anshu Agarwal, general partner, Converge

What kinds of investment opportunities are you looking for right now?

We are investing in LLM applications and infrastructure, also companies building foundation models using the same underlying techniques as language models but applied to domains other than language. This space is very nascent and very promising. Automation tech leveraging AI is another area of interest.

How do you prefer to be approached: a cold email, a warm intro, or another method?

Warm intros are always good, but anyone can reach out to me via LinkedIn messaging.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

For some aspects of building generative AI products, no one can claim to have much experience, because the space is so new. Companies innovating at the application layer on top of OpenAI need to do a lot of prompt engineering, which a year ago wasn’t even a discipline. At the application layer, domain expertise trumps LLM usage ability, which can be learned.

However, we observe that many companies, even those that also use OpenAI, build proprietary machine learning models as part of their product. Some companies are building infrastructure for training, orchestrating, and governing AI models. Others are developing their own foundation models in various domains. AI expertise is needed for all of it, and therefore seasoned AI talent will continue to be in high demand.

Generally speaking, how much salary should the founder of a pre-revenue startup in a Tier 1 city pay themselves?

Sometimes founders may not take a salary if they have years of experience and have saved from previous companies/startups. But if they haven’t, they definitely need to take a salary, [and] it should be somewhere between 100,000 and 150,000 and that is usually sufficient to sustain in Tier 1 cities.

In August 2023, what are some of the top questions founders need to ask investors?

  • Has the investor been in the founder’s shoes? How successfully?
  • How many startup journeys have they seen, and over how many tech and economic cycles?

What’s a traditional pitch tactic that no longer works but is still a common practice?

Sometimes founders create an artificial sense of urgency for prospective investors, which can backfire and make a founder look inexperienced.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

A traditional pitch still works because it provides background to an investor who is probably spending 30 minutes to an hour to figure out if it is interesting. So key points should be addressed: clear definition of the problem, your solution, why is this problem solvable now, what is your moat, why you are the team to solve this, some idea about go-to-market, how much funds you are raising and use of funds.

I am very open to reviewing pitch memos if it addresses the main points above.

What are you reading/watching/listening to right now?

Watching “Ted Lasso,” season 3. Perfect example of how a company can win even if they don’t have “star power.” It’s teamwork, hard work and investor support that leads to success.

Kittu Kolluri, founder and managing director, Neotribe Ventures

What kinds of investment opportunities are you looking for in August 2023?

We invest in breakthrough technologies that stretch the imagination or simply put — deep tech companies doing something net new. About 60% of our capital goes into companies in the software space, including enterprise security and infrastructure, fintech, web3, and 40% goes into companies leveraging information technology, such as clean energy, AI and robotics, computational biology and more.

In terms of stage, we typically invest in early-stage companies and will lead or co-lead a seed or Series A. We also invest from our growth-stage fund, Ignite. This is reserved for more mature companies with evidence of product market fit and we’ll come in at a Series B or later.

How do you prefer to be approached: a cold email, a warm intro or another method?

In general, I prefer a warm intro from somebody I know within my network since it provides an initial screening process. That said, two out of the 50 companies Neotribe has invested in came from completely cold emails. In those cases, the founders were able to immediately grab my attention and establish some credibility with me because they effectively outlined their body of work and background in their initial email.

Many laid-off engineers are launching their own startups: What are some of the skills/experience you look for in nontechnical founders?

Given the nature of our investments in deep tech, these companies are solving hard technical problems so we usually need at least one technical founder. That said, it can be useful to also have one nontechnical founder given that technical founders generally don’t know how to go about looking for product market fit.

We would be looking to the nontechnical founder to have experience in bringing a product to market, sales and marketing. At the early stage of a company it’s not a little bit about product-market fit; it’s all about product-market fit. The nontechnical founder needs to be the one that can help discover product market fit for the company and take on that leadership role.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

While you don’t need to be an expert in the internals of artificial intelligence, some understanding and experience with AI concepts such as supervised learning, unsupervised learning, and generative models is important.

An understanding of how training data, model selection and tuning, and model hallucination can impact results is critical. Domain expertise and proprietary data in your vertical could give you a competitive advantage in using generative AI effectively.

Generally speaking, how much salary should the founder of a pre-revenue startup pay themselves?

It all depends on where the founder is in their personal life. Are they married? Do they have a mortgage or other financial obligations? I’m empathetic toward having a reasonable salary based on these factors. In general, I’ve found most founders will pay themselves around $150,000 or less; $200,000 may be appropriate in the right circumstance, but $300,000 is ridiculous.

In August 2023, what are some of the top questions founders should be asking investors?

“Are you actively investing?” In venture, if you’re just starting a company at the seed stage, there is very little capital available because they don’t know what the market will be at the growth stage. If you’re looking for Series A or B, ask investors if they are looking to invest at that stage and what do they typically look for? It’s about product-market fit with the investor, not just with the customer. The company is a product that the investor is buying — so founders should be asking each investor they speak with what they are looking for.

I’ll also add if you’re a founder planning to reach out to an investor in August, keep in mind people tend to be out of the office longer than usual this time of year. I suggest reaching out right before Labor Day to set up a meeting in September or wait and start your outreach altogether [next month].

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I’m open to pitch memos, and I’m even open to reviewing an executive summary. In fact, it’s more time efficient for me. I can quickly tell if the company has product-market fit with me because we are clear on what our investment model is.

Usually when a company sends a deck, I have to type in my email just to open it and I often find with the extra steps I end up never reading it. Investors receive a lot of emails, so your elevator pitch can’t take more than two floors. You have to quickly relate to the investor and tell them why your company is exciting, why you and why now in a short period of time.

Tell us about the best pitch you’ve received recently: At what point in their presentation did you realize you were going to invest?

I’ve never decided to invest in a company during an initial presentation. When we first meet a company, sometimes there’s a fast-path reaction. When you listen to the pitch and you say to yourself, “Why didn’t I think of this?”

But you’re not ready at that moment to say I’m going to invest because then the slow path kicks in and that’s when we take our time to do our diligence. We always make sure the slow path validates the fast-path reaction, and if it does, that’s when we decide to invest. We’re investing people’s penchants, endowment savings, etc., so we take it very seriously and we never make an impulse decision.

What are you reading/watching/listening to?

  • Reading: “The End of the World Is Just the Beginning: Mapping the Collapse of Globalization,” by Peter Zeihan
  • Watching: A lot of sports and Jack Ryan (Season 4) [Amazon Prime]. I also just finished “Sleeping Dog,” a German crime thriller series on Netflix. I enjoy watching shows in other languages because it’s usually quality content if it has been cherry-picked by Netflix and it gives you a better sense of other cultures.
  • Listening to: “The Drive” podcast hosted by Dr. Peter Attia and “The Huberman Lab” podcast hosted by Andrew Huberman. Both discuss science-based tools to increase longevity.

Jennifer Lee, partner, Edison Partners

What kinds of investment opportunities are you looking for right now?

We invest in growth-stage technology businesses. While there’s more discipline these days among both startups and investors, regardless of the macroenvironment, we are always excited about capital-efficient businesses with strong unit economics and fundamentals across enterprise software, fintech and healthcare IT.

How do you prefer to be approached: a cold email, a warm intro, or another method?

I actually don’t have a preference: I’m open to both a warm intro and a cold email. For me, what’s more important than the approach is the actual content.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the

team?

I don’t necessarily have a “bar” for expertise, because each company is different and evolving at different stages, depending on said use case. That said, ideally there is some level of domain expertise in-house, either getting a better understanding of how to apply generative AI in your business and your industry, or implementing and productizing a specific use case, or monetizing with a full business model.

In August 2023, what are some of the top questions founders need to ask investors?

What is exciting to them about the type of investments that they make? How do they think about capital formation and is that aligned with the way that you’re thinking about your own capital formation of the company?

In addition to capital, find out what value creation resources and support they offer to their portfolio companies, from the board and governance level down to the operating day-to-day, and how the investor can help guide your company’s growth post-investment. How will the investor partner with you in this capital partnership? That’s the real question both parties should be able to answer.

What’s a traditional pitch tactic that no longer works but is still a common practice?

What doesn’t work is the high-level, standardized, walk-through-the-deck and a simple sales pitch only. The best pitch to me is conversational and when I feel that the founder is being genuine and authentic and not necessarily telling me about only the company’s positive aspects.

What are you reading/watching/listening to right now?

I’m reading a novel for a change: “Independent People,” by Nobel laureate Halldór Laxness.

Dave Zilberman, general partner, Norwest Venture Partners

What kinds of investment opportunities are you looking for in August 2023?

Our early-stage enterprise team remains focused on investing in innovations for the modern enterprise stack, developer solutions, applied AI, and cybersecurity. We’re especially intrigued by the magnitude of enterprise solutions needed to leverage AI applications in a responsible and safe manner.

Established verticals such as role-based access control (RBAC), data loss prevention, and data privacy, in particular, need to evolve and pivot to support this new AI vector. In the face of growing restrictions around AI usage, we see a significant opportunity to invest in reliable, secure, and compliant infrastructure so large enterprises can take advantage of these powerful AI solutions in production (not just experimentation, as most AI solutions are currently being used).

How do you prefer to be approached: a cold email, a warm intro or another method?

I always prefer warm introductions. Between public listings of our portfolio companies (for which the executive team, board and co-investors are easy to identify) and LinkedIn contacts, Norwest keeps a public profile that founders can leverage to identify first- or second-degree connections.

Extenuating circumstances could necessitate a cold email, but the ability to network is a foundational skill set for founders, not just for finding investment partners but also for hiring top talent and securing customers.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

The low barriers to building AI applications are liberating for application providers, but they also create massive noise and competition. As such, go-to-market experience is even more valuable than ever for AI application developers. For AI infrastructure and security companies, domain experience from security and selling into enterprise environments is very important.

What are some of the top questions founders should be asking investors?

  • What’s your point of view (or thesis) on this sector?
  • Have you spoken to our competitors? How do we stack up?
  • Ask a tactical question (e.g., sales, marketing, hiring, HR) that you’re wrestling with to see if they have a valuable point of view.
  • How many boards are you on?

What are you reading/watching/listening to?

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I strongly prefer slides. Reading a long memo is cumbersome and I’m not evaluating founders on their ability to write in prose.

What’s one traditional fundraising tactic that founders should remove from their toolkit — something that no longer works but is still a common practice?

I’ve observed an increasing number of first-time founders pitching us as if they’re on “Shark Tank,” providing a high-level vision with few specifics and indicating outright that they’re raising X dollars for Y percentage of their company.

I advise founders to let investors decide if they’re intrigued before potentially discouraging them with valuation, especially one that may not be reflective of market conditions. One may be overestimating or potentially underestimating the valuation, which can result in more challenges down the road.

Jake Jolis, partner, Matrix Ventures

What kinds of investment opportunities are you looking for right now?

My ideal investment right now would be to lead a Series A in a product leveraging synthetic voice at its core. Large language models work great for written text. Voice still has this universe of tricky user experience problems that underlying infrastructure is just on the cusp of solving, such as latency and cost, so the opportunity is very much still there and the use cases are many.

How do you prefer to be approached: a cold email, a warm intro, or another method?

Warm intro!

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

Not much, to be honest, if you’re building for most of the app layer and you’ve got a stellar software team. Most founders should dig a more “traditional” moat (e.g., brand, GTM/distribution, network effect, data advantage, exclusive partnerships, etc.).

My motto on generative AI stuff is that your model is not your moat. At the app layer, founders can now leverage an incredible set of third-party tools and models. The open source stuff, especially spearheaded by Meta, is changing the game for everyone and putting tons of positive pressure on the closed source providers like OpenAI, etc.

I’ve backed PhDs from FAANG companies as well as dropouts. The experience you need depends on what layer of the stack you’re innovating.

Generally speaking, how much salary should the founder of a pre-revenue startup in a Tier 1 city pay themselves?

In those early days, the number should be enough that you worry about your startup and not food/bills/rent. That said, it seems like this has really gone up since my founder days . . . we paid ourselves the legal minimum wage, to meet the minimum required to qualify for health insurance.

I’m looking at Pave data right now and it says the average today is $150,000; maybe that’s what folks need in 2023? It seems higher than what I’m hearing for seed-stage funded companies anecdotally.

In August 2023, what are some of the top questions founders need to ask investors?

For prospective investors you’re evaluating, you’re better off calling up founders they’ve worked with in the past and asking how the investor has helped them.

For existing investors who know you well, ask them what they worry about most that could prevent your company from raising the next round, and — if they’re good — involve them in a discussion about how to go about de-risking that thing.

What’s a traditional pitch tactic that no longer works but is still a common practice?

FOMO-driven, artificially short time periods, minimizing opportunity for diligence.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I love pitch memos. I tend to print them out on paper.

Tell us about the best pitch you’ve received recently: At what point did you realize you were going to invest?

Probably Basedash’s product demo. The founder connected an SQL database and Basedash returned a fully functional, editable — and beautifully designed — custom admin panel ready to use. It literally looked like magic, but of course it’s just a very clever use of large language models.

The AI infers the meaning of column names in the database schema with no PII shared. Just works in the background with all the complexity obscured from the user’s view. At that point I decided to lead the seed round.

What are you reading/watching/listening to right now?

“Exploding the Phone” by Phil Lapsley, about how a group of teenagers in the ’60s hacked AT&T to make long-distance landline phone calls for free. It doubles as a history of telephony.

As for listening, I keep coming back to Hôtel Costes’ playlists. It’s this Parisian hotel that plays such unique house-y, tropical-y, jazzy lounge music that their playlists have amassed a pretty big Spotify following these days.

Chad Cardenas, founder and CEO, the Syndicate Group (TSG)

What kinds of investment opportunities are you looking for right now?

We’re looking for companies with a solution that is a must-have (not just a nice-to-have) for the majority of global 2000 enterprises, if not in cyber, then a disruptive tech in traditional infrastructure and we’re curious to understand how a company may be using AI to enhance their offerings. We also look for companies that have a long-term, channel-focused go-to-market mindset.

How do you prefer to be approached: a cold email, a warm intro, or another method? 

Warm intros coming from a trusted source are typically better.

In August 2023, what are some of the top questions founders need to ask investors?

  • What is the clearly articulable technical differentiation?
  • How do you plan to achieve scale at speed in a hyper-competitive market?
  • Why is the current team well-positioned to execute on the growth strategy?
  • What does an ideal strategic ecosystem look like today, a year from now, three years from now?  What’s to keep a larger incumbent player in your space from building or acquiring a similar solution?
  • What is the total addressable market, and explain in detail how you arrived at that number?
  • Is the tech a must-have or a nice-to-have for the majority of enterprises?

What’s a traditional pitch tactic that no longer works but is still a common practice?

Some founders are too attached to original ideas and can’t see when to pivot to bigger opportunities. Be open to the possibility that you don’t have all the answers and there may be a better path for your business that you hadn’t previously considered.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

Open.

What are you reading/watching/listening to right now?

Matthew Kinsella, managing director, Maverick Ventures

What kinds of investment opportunities are you looking for right now?

I am looking for early-stage startups in cybersecurity, AI, and quantum technologies. I’ve always been a fan of investing in cybersecurity, as it’s a derivative play on any large paradigm shift in technology. Just like the shift to the cloud enabled the creation of many new, iconic cyber companies, generative AI advances will create the need to further secure organizations’ data, as well as utilize gen AI to help cybersecurity professionals do their job more efficiently.

How do you prefer to be approached: a cold email, a warm intro, or another method?

Warm introductions are best for me — it’s always great when we have someone in common and have a starting point for a conversation. That said, if a founder knows something about me or Maverick and thinks we could be a great fit as an investor, please definitely reach out!

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

If the company is deep in the AI infrastructure layer, then I think they would likely need to be deeply technical, or at least be paired up with a deeply technical co-founder. But if the company is utilizing LLMs to enable an application to solve a less technical business problem, it’s probably more important that the founder have deep experience in the problem they are trying to solve as opposed to being super technical.

What’s a traditional pitch tactic that no longer works but is still a common practice?

Nonpersonalized cold-emailing rarely works. If you’re going to go the cold-email route, I’d advise making it as personalized as possible. And if you’re going to use a mail merge, make sure it actually has the name and not [insert name]. Haha.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I’m open to reviewing pitch memos and a particularly big fan of doing a short walkthrough session with Loom. Efficiency is key here for the initial pass and to understand the business. After that, efficiency is the opposite of key, as I like to spend as much time as possible with the founder if we’re getting serious about investing.

Tell us about the best pitch you’ve received recently: At what point did you realize you were going to invest?

The best pitch I received recently was from someone who I had worked with in the past at a prior company. He is a deeply technical person and uncovered some challenges in training DL models as he was working on them. He then started creating a product to help with this problem. He’s an example of “the founder being the product.”

What are you reading/watching/listening to right now?

It’s not the lightest read, but I’m currently working my way through the “The Age of Napoleon: The Story of Civilization, Volume XI” by Will Durant, someone I consider to be the “original LLM” of history — he basically learned all the knowledge there was to know! After over 30 years, he then wrote an 11-volume history of humanity, starting with ancient Sumeria and ending with Napoleon.

After he finished his 11-volume series, he wrote a short, 100-page book called “The Lessons of History,” in which he summarized all he had learned. Not unlike asking Chat GPT to “summarize history and give me the big takeaways about humanity!”

I’ve also been reading “The Qualified Sales Leader: Proven Lessons from a Five Time CRO” by John McMahon, which I definitely recommend for those building sales teams.

Ty Findley, co-founder and general partner, Ironspring Ventures

What kinds of investment opportunities are you looking for right now?

Our sector-focused fund focuses on industrial supply chain innovation (manufacturing, construction, transport and logistics, and alternative energy), and a major topic of discussion right now coming out of both COVID aftereffects and rising global geopolitical tensions is nearshoring the U.S. domestic supply chain.

We’re looking for founders who also see the need for productivity, security, and sustainability solutions applied to the massive cross-border GDP flowing between the U.S. and Mexico border that will be critical for the thesis behind reshoring to work. See our research, “Nearshoring: A Shift in LATAM Transport & Logistics,” that we released publicly in August.

How do you prefer to be approached: a cold email, a warm intro, or another method?

We respond to all emails, but doing advance homework on our team members and finding a way to network via a warm introduction is always preferred (also shows us the grit/hustle that is a key skill for founders!). Our team can also be reached via our website.

In August 2023, what are some of the top questions founders need to ask investors?

Ask them where their fund is in its lifecycle (do they have dry powder to deploy?). Ask them to introduce you to several founders they’ve worked closely with who have both succeeded and failed (i.e., how do they show up when times are good and when markets reset?).

Ask why they are genuinely passionate about supporting the problem your company is trying to solve (do they have sector and/or market experience to help you scale?). Ask them what success looks like (i.e., small and large funds have different incentive alignments).

What’s a traditional pitch tactic that no longer works but is still a common practice?

I have nothing but sympathy for founders out there that are in the arena trying to make it happen and I will take a pitch in any form they think is best for them to shine. As always, though, don’t try to pop up and give an artificially short timeline in the hopes of driving FOMO . . . two- to three-week shotgun marriages are coming back to bite founders right now.

What are you reading/watching/listening to right now?

I’m rereading Annie Duke’s book “Thinking in Bets.” It’s all about making smarter decisions and thinking in a more probabilistic fashion (not black and white), and I think the tactical tips it provides are applicable to anyone. I’m fortunate to serve on an Ambassador Council at the nonprofit she co-founded, the Alliance for Decision Education.

Kathleen Kaulins, principal, Plymouth Growth

What kinds of investment opportunities are you looking for right now?

Plymouth invests in growth-stage technology companies in historically underinvested geographic markets. Specifically, we invest in mid-continent B2B SaaS and tech-enabled services companies with $3 million to $10 million in revenue, proven business models, and capital-efficient growth plans.

We look for investment opportunities that are poised for growth and would benefit from a partner that has experience scaling companies to enable these businesses to achieve their goals more quickly.

How do you prefer to be approached: a cold email, a warm intro, or another method? If you’re comfortable doing so, please share your contact info.

A warm intro definitely helps elevate a request to connect and shows initiative on the part of the founder, but more important than the medium for delivery is the message itself.

You can reach me at kkaulins@plymouthgp.com or you can also connect with us through our website.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

Without team members who possess a detailed understanding of the different AI technologies, their respective strengths and limitations, and which might be best suited for certain use cases, companies run the risk of getting caught up in the hype and trying to implement the wrong technologies, ultimately wasting time and money for the organization. It is also important to note the rate at which AI technologies continue to evolve themselves require companies to cultivate talent that has a willingness to learn and expand their knowledge.

Determining the right level of expertise and experience will ultimately be dependent on the types of AI projects a company is looking to implement. If it is not feasible to have some of these skills and capabilities in-house on a full-time basis (e.g., data scientists with particular experience in statistics), it will be important for companies to connect with services providers or consultants who do have the required expertise.

In August 2023, what are some of the top questions founders need to ask investors?

It is critical that founders take the time to understand the motivations and behaviors of potential partners, as well as the value they will be able to provide.

One of the best ways to do this is to ask investors to speak with founders they have previously worked with (not dissimilar to the reference checks investors do on founders themselves!). Founders should particularly ask investors to speak with individuals at portfolio companies where things did not go as planned. Understanding how investors act in these scenarios can be informative when making a decision around a potential long-term partner.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

Our investment team will review both formal pitch decks as well as pitch memos. The key is making sure that the document is concise and includes the relevant information to help investors make an efficient decision around whether the current opportunity is a fit with their mandate.

Tell us about the best pitch you’ve received recently: At what point did you realize you were going to invest?

One of the best pitches I received recently was by a founder who was very upfront about the challenges they face with their business in early conversations. The fact that this founder was upfront and transparent around areas of the business that were facing challenges was refreshing and also showed a high degree of awareness on their part.

What are you reading/watching/listening to right now?

I am rereading a favorite book, given the challenging and unpredictable operating environment we’ve seen over the last few years: “The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers,” by Ben Horowitz.

Ultimately, I love this book because it serves as an important reminder to first-time founders, seasoned entrepreneurs, and investors that building a company is really hard work and that there is no clearly defined path or recipe for success.

Samarth Shekhar, EMEA regional manager, SixThirty Ventures

What kinds of investment opportunities are you looking for right now?

Our focus has been and remains on B2B/SaaS startups at the intersection of finance, health and privacy: areas that continue to offer large, often global markets to bold founders building meaningful businesses. We look for startups across fintech, insurtech, digital health and privacy, from pre-seed to Series A/B stages, though typically post-revenue and first few (enterprise) customer; and for founders who are going after massive problems or opportunities in specific sub-sectors or business areas.

We are especially well-placed to help startups step up their go-to-market approach, sales, pricing, etc., enabled by our platform that brings together our corporate LPs, comprising category-leaders in banking, insurance and healthcare.

How do you prefer to be approached: a cold email, a warm intro, or another method?

I would love to get a warm intro, but having been an enterprise sales guy myself in my previous life, I’m always open to a clearly written LinkedIn outreach or email (samarth@sixthirty.co).

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

While financial services and healthcare have been power-users of AI/ ML, using them in lending, investments, insurance, etc., generative AI has opened a Pandora’s box. In the short-term we are actively looking for companies that can help banks and insurance companies batten down the hatches against threats and risks, bias, unfairness or adversarial attacks, etc. We are scanning opportunities in the application/vertical-specific solutions/API layers (rather than, say, the hardware, infrastructure or model layers) that can help financial institutions test and deploy generative AI, starting with areas that are noncritical or noncustomer facing.

Generally speaking, how much salary should the founder of a pre-revenue startup in a Tier 1 city pay themselves?
I would say just enough to get by without worrying about the basics — so say €40,000 to 60,000 here in Europe if the founder’s financial situation permits, though this would indeed vary based on other factors.

In August 2023, what are some of the top questions founders need to ask investors?

Top questions, roughly in order:

  • Are they actively investing? If yes, do they lead or follow, their typical ticket size and qualifying criteria (e.g., post, revenue, specific ARR cut-off) if any?
  • Does the idea align to their sweet spot (sector, geography, revenue model, go-to-market approach, etc.), and why is it a good fit/how can they add value?
  • What does the due diligence and decision process look like, and what are associated timelines and next steps?

What’s a traditional pitch tactic that no longer works but is still a common practice? Are you open to reviewing pitch memos, or do you prefer a completed deck?

I would say trying to get investors on a call without sharing the deck or teaser, or expecting them to sign an NDA beforehand. A completed deck is preferred.

What are you reading/watching/listening to right now?

Zamir Shukho, founder and general Partner, Vibranium Venture Capital

What kinds of investment opportunities are you looking for right now?

As a fund, our focus is on investing in B2B SaaS companies. Currently, we have identified four verticals that particularly interest us: productivity software, financial services, sales and marketing, as well as media and information services. Naturally, having AI integrated into their product would be a significant advantage for any startup teams in these areas.

How do you prefer to be approached: a cold email, a warm intro, or another method?

The optimal approach to connecting with our fund is by completing an application form on our website. This ensures that the startup is promptly entered into our CRM system, initiating the evaluation process with our team.

If you’re comfortable doing so, please share your contact info.

If you wish to contact me directly, you can do so through email or LinkedIn.

We seem to be in a generative AI hype cycle: Where’s the bar set in terms of expertise/experience with AI, and how much domain expertise do you need on the team?

Recent statistics have indicated a significant decline in AI funding during Q2 2023, with a drop of more than 40% in funding for new companies entering the market. Therefore, we are cautious about making hasty judgments and getting caught up in hype. Startups that emphasize their AI capabilities should demonstrate strong internal domain expertise and have at least a senior developer with the knowledge to build robust AI products.

In August 2023, what are some of the top questions founders need to ask investors?

Startups should inquire about investors’ follow-on strategies and how they intend to contribute to founders’ business growth beyond merely providing financial investment. It’s important to determine whether investors are willing to leverage their network, connections, and expertise to facilitate opportunities and help in building a more robust team for the startups.

What’s a traditional pitch tactic that no longer works but is still a common practice?

I would recommend that founders not excessively emphasize perfecting the pitch. Instead, they should focus on building a comprehensive data room and ensuring they are well-prepared with robust answers for any potential questions.

Are you open to reviewing pitch memos, or do you prefer a completed deck?

I believe a good initial approach could involve presenting a concise one-page summary to representatives of the fund’s team, such as a scout or an analyst. This step can help ensure that your offering aligns with the fund’s profile and investment focus. If this initial assessment yields a positive response, you can then proceed to send your complete pitch deck for a more thorough review and analysis.

What are you reading right now?

My older daughter started high school: I’m reading “The Parents’ Playbook for Raising Character Leaders” by Joseph L. Thomas. The book provides insights into how parents can foster their children’s growth in sports and athletics, which is particularly relevant as all our kids are involved in various sports.