Author: MartinGTobias

Goldilocks: Adjective: “having or producing an optimal balance usually between two extremes.”

I am often asked “What stage do you invest?” While most people expect to hear “Pre-Seed”, “Seed” or “Series A, B, C, etc”, I answer “The Goldilocks Stage”. Traditional Venture stages have become a function of fund size and seem to be increasingly disconnected from any thesis around long term value creation. When you start to look for the Goldilocks Stage, you will find it everywhere; Early-stage venture, mid-stage, Growth stage, IPO, and the public markets.

Every investment I have ever made with a 10x or more return was in the Goldilocks Stage. Here is how I define it:

• Goldilocks Stage: “The “just right” mix of value-creating innovation balanced with a clear path to profitably fulfilling a fast-growing customer need.”

When you invest in the Goldilocks Stage you fund a clear set of milestones intended to move the company up the path of product innovation and customer adoption to the next logical inflection point. In the Goldilocks Stage Innovation = Customers. The ultimate goal of every company which hopes to continue to grow should be a self funding loop of Innovation = Customers = Innovation = Customers…. ad infinitum. For a master class on this see: Amazon, Apple, Google, Tesla, etc. Companies stall when they either stop innovating or fail to find new customers. For a master class on this see: General Motors, General Electric, most Oil majors, etc.

Less than 5% of the deals we see at Incisive Ventures are raising funding in the Goldilocks Stage targeted at BOTH customer and innovation growth. Many companies are mainly funding ONE side of the equation which, while it may lead to up rounds, rarely leads to long term sustainable growth and the virtuous self-funding cycle. Make these one-sided investments at your peril.

Two scenarios we commonly see include:

• The Overnight Unicorn or Brand Project.
  • 
  • In this scenario, minor innovation gains wild adoption quickly. With massive adoption numbers, investors pour funds into customer acquisition and expansion, often times before the business model has been fully flushed out. While there have been many examples of investors making money in these deals, most have flamed out when customer growth stalled and there was no new innovation to reach new customers.
  • Examples include:
    • Bird. One of the fastest companies to >$1B valuation in the history of venture. Investors funded an aggressive expansion based on initial traction. The innovation was very thin: Off the shelf scooters with a booking/billing app and some access control hardware. Investors funded brand building and building the network over innovation.
    • Honey. Making a browser plug in which automatically tried coupons was a very thin innovation, but it got massive customer adoption because it removed all the searching, copy and pasting of coupons (the friction). Investors piled in behind huge adoption numbers.
    • WeWork. Co-working was around long before WeWork. There was little technology innovation and heavy investment in brand and fund negative returns to gain customer share, hoping to make it up in the end.
  • The primary risks in Overnight Unicorns include:
    • Lots of competitors. Since there is little innovation, these concepts can be copied easily and must rely on brand and customer loyalty for profits. With lots of competitors, margins get squeezed and many times no-one in the category is making profits.
    • Stalled customer acquisition. Either because the market gets saturated, or because competitors come in and compete for customers. When the valuation is based on rapid customer growth, and that stalls, even reverts, bad things happen.
  • The right kind of Overnight Unicorns:
    • The power law in venture investing gains much of its power from the fact that companies creating new categories, tend to get an outsized percentage of the market and valuation multiple. If a company is truly creating a novel category, sometimes focusing on customer/market share is the right initial strategy when balanced with delivering innovation over time which delivers increasing value to the market.
    • A classic example of this is Facebook. They focused on fairly simple community technology at first and drove massive audience growth. When they went public they had barely turned on advertising. They kept up the innovation internal and through M&A (WhatsApp, Instagram, etc.) as the audience also grew. This pushed the company back into the Goldilocks stage.
• The Science Project.
  • 
  • In this scenario, the company falls down a feature rathole or bites off a problem too expensive to solve within their funding window versus the value delivered. Valuation is driven by product progress, patents, hiring smart people, etc. rather than customer traction. One can also find cases where investors made returns with science projects, it is typically through acquisition by a company with access to customers rather than as a stand alone entity. There have also been spectacular flame outs when the end product could not profitably find a large enough market. Product development always costs more and takes longer than the budget, these deals can easily outrun their funding runway.
  • Examples include:
    • Virgin Galactic. The story has romantic appeal, the founder is charismatic, they have been at it for 10 years and don’t have a clear path to success. Even if they can successfully fly, how big is the market for space tourism really?
    • Nikola Motors. Another appealing story “The Tesla of trucks” with a charismatic founder. But building trucks is hard, they can’t decide on the fuel source, outsource most of the production, and there are weird accounting things. Oh and Tesla has its own commercial truck planned and a track record of delivering products (albeit a bit late).
    • Theranos. Sometimes when developing a very hard product, the pressure to show progress can be so great that companies actually lie to investors. Investors believed the made up progress and promise of big market. The product never worked. We know the ending.
    • Juiceroo. I was never lulled by the idea of a $400 juice box squeezer. Plenty others were. I love the hardware teardown which exposed how over-engineered the device was. Copious investor dollars spent to do something the human hand could do for free.
  • The primary risk in Science Projects include:
    • Overrunning the funding window. If you can’t ship a product on the capital you have raised, you depend on investors to believe more development will lead to a product in the future. Cost over runs can ruin a funding window.
    • Building the wrong product. Without customer feedback, engineers build what they think the market wants, or more typically what they want. There is often a dis connect.
    • Not getting final approvals. Many products, even if they work, require regulatory or market approvals to go on sale. Often companies don’t budget for this step correctly. Or the regulators require re-work, more tests, more trials, etc. driving up product development.
    • Scientist who can’t sell. Doing science and selling are very different worlds. When a product is finished and the company pivots to selling, many times they put the scientist in front of customers, which only works in certain industries. Managing product development is very different than managing sales. It is hard to be great at both.
    • Market changes during development. I was once an investor in a software company building an operating system for a new class of Intel network operating chips. The company had a contract with Intel to install the software on all chips. But Intel ran into manufacturing and scaling problems with the chips and canceled the project. No chip, no software, no possibility to pivot. More frequent is that someone else solves the hard problem in a different way, or before your product is finished and gets to market before you. Then you are not the innovative leader, you are following. Remember the Sony BetaMax which was way better than the VHS recorder? Didn’t matter, the VHS solved recording TV around the same time in a cheaper and more easy to use way. Problem solved, superior engineering be damned.
  • The right kind of Science Projects:
    • Science projects must eventually deliver a product that customers value, are willing to pay for, and that product must reach customers at a level which overcomes the development costs. There are typically two ways to achieve this:
      • Sell to a company with market access. This is the primary business model of biotech firms. Do science for years, then sell to big Pharma who has sales reps to reach the market and get regulatory approval. For a long time this was also the model in networking equipment. Make a new box, sell it to Cisco.
      • Get customers. The pivot from science project to selling is very hard. Companies that want to create a self-funding innovation machine need to good at both developing and selling products.
    • Be wary of companies that say their patents will be valuable and protect them. There are very few examples of patents creating long term value, too many ways to get around them with a different approach.
• Is investing in Goldilocks Stage a guarantee?
  • 
  • No. But I have had better returns over time than any other stage. When writing a check into what they think is a Goldilocks stage, an investor must be right about three things:
    • Market trend. The size and shape of the market for the product. How it is growing, how to reach the market, etc.
    • Product innovation trend. Can the company build the product given the resources in the round you are investing in. What is the next product? Is there a pipeline?
    • Management ability. Can management find the right product/market fit within the funding window you are funding? Have they shown a proven ability to pivot and do what it takes to stay in the zone?
  • How to identify the Goldilocks Stage?
    • Spend 25 years angel investing, and you probably will be above average at it. It takes alot of investing in the wrong stage and behind the wrong signals to find the ones that correlate to returns over time. So, yea, make alot of mistakes and learn from them. At the highest level, spend your diligence time on the three areas you have to be right about, market, product, and management. And be right about the FUTURE trends in these areas, do not assume prior performance will continue into the future.
  • What can go wrong with Goldilocks phase?
    • You could be (and likely are) wrong about one or all three of the above. Product can stall. Market can stall. Management can fail to execute. Those risks are why you have the opportunity, if right, to make an outsized return.
    • Many companies start out one way then end up another or go in and out of the Goldilocks phase. Whenever a company presses too hard on one side of the equation at the expense of the other, stalls tend to happen. So ensure progress on both market and product growth while management stays focused on execution.
• There is a Goldilocks Stage. It is the “just right” mix of customer traction and product innovation, both of which will continue to grow a meaningful amount during the funding window of the round you are funding. Invest in Brand or Science projects with caution and if you do, have a plan with management to move into the Goldilocks Stage. To follow along with deals Incisive Ventures believes are in the Goldilocks Stage, join us.

Have. you ever had a conversation with someone only to find out later that the two of you took away totally different meanings from the exact same conversation? I have found that many times the root of the dis-connect is different definitions of key qualifying terms used in the conversation. The same words can mean vastly different things to different people. This is especially true with words that qualify something in terms of a probable outcome: the Probability Terms. Explicitly stating your own numeric probability assignment for each of the “squishy” terms and communicating that to people ahead of time, can significantly reduce dis-connects and mis understandings. I found this helpful tool to do just that. They have a data set of a couple thousand responses, so the confidence interval of each term fairly represents the range of outcomes you would find in common conversation partners. Listed below are the numerical probabilities I personally assign to each general Probability Term commonly used.

Why this is important when talking about Investments? If I write in a deal memo there is a “Real Possibility” of the company closing a big deal in the next two quarters, what does that really mean? Based on the results of the Probability Survey, the common understanding of “Real Possibility” is between about 38% and 75% numerical probability. That is a huge range! If I am a 38% person talking to a 75% person, we are going to come away with vastly different understandings of the conversation. At Incisive Ventures when I write “Real Possibility”, I have assigned a 57% probability to the outcome. A “Serious Possibility” is 70%. If you ever have any question as to what the EXACT probability of an outcome is when we use one of these terms, please consult this post. Being precise is incisive.

These Probability Terms and the associated numerical probability values are a way to be precise about our opinions of potential outcomes base on our knowledge at the time we make the statement. Of course there is no guarantee we are right. There is always a greater than zero chance of different outcomes. Even when we say something may “Never” happen, we assign a 1% chance that it may. Investing is always a game of incomplete information with a variety of possible outcomes. While we endeavor to be precise, we do not have perfect information on how the future will unfold, no one does.

• Incisive Ventures Probability Terms and associated numerical probabilities:
  • Term
    • Probability
  • Always
    • 99
  • Certainly
    • 97
  • Slam Dunk
    • 95
  • Almost Certainly
    • 93
  • Almost Always
    • 85
  • With High Probability
    • 80
  • Usually
    • 77
  • Often
    • 75
  • Serious Possibility
    • 70
  • Likely
    • 67
  • Frequently
    • 65
  • Probably
    • 60
  • Real Possibility
    • 57
  • More Often Than Not
    • 55
  • Possibly
    • 51
  • With Moderate Probability
    • 40
  • Maybe
    • 35
  • Might Happen
    • 33
  • Not Often
    • 30
  • Unlikely
    • 20
  • With Low Probability
    • 10
  • Rarely
    • 5
  • Never
    • 1

Angel investing is a team sport. Many Limited Partners, Founders, friends across our larger network have asked how they can help bring the best companies to Incisive Ventures.  Our answer is the Incisive Ventures Upgraded Scout Program. 

When you help us source a great company we invest in, we share the carry and you get more money into a company you love.   Anyone can be a Scout, the only requirement is that we invest in a company you introduced to us that we didn’t otherwise know. We prefer seed and pre-seed, but will consider any stage and any geography as long as there is a good fit with our Meta Themes.

How to Scout for IV:

• Send us an email making your incisive, personal case for why this investment meets our Meta Themes and would fit through our funnel. Be sure to include:
  1. The size of your personal check.
  2. 3-6 bullet points similar to the TL;DR section of our investment memos.
  3. Your personal insight to Management, product/market fit, traction, and co-investors. 
  4. Explain how the company fits into our Meta Themes, from your perspective.
• We will review and tell you if we want to move forward typically within a week.

Benefits of being an IV Scout:

• With the IV backing, you get more money and our value added network dedicated to companies you have a high degree of conviction on.
• We share our syndicate carry as a success fee when we invest within 3 months of the introduction.

If you are connected to a great company that fits our Meta Themes and how we filter the funnel, send it over! Become an Incisive Ventures Scout. The team wins.

Incisive Ventures reserves the right to update terms and conditions for the Scout Program at any time. Current program details here.

PS: Another hat tip to Peter over at Unpopular Ventures for the inspiration of this syndicate upgrade.

PPS: Why a picture of a truck? I love them! International Harvester Scout.

Had fun talking start up investing with Todd on this podcast.

Angel Syndicates have been a huge upgrade to the early-stage fundraising ecosystem delivering over $3B in capital recently and the pace is accelerating. Syndicates promise to add value and reduce friction for both investors and companies. Unfortunately, as an investor in over 300 syndicates, I have often been underwhelmed and frustrated. So I decided to upgrade the Syndicate process with Incisive Ventures.

Over 25 years of investing and as a CEO, I have directly invested in over 90 companies, am an LP in 12 Venture funds, have been a Venture Partner at a major fund and raised over $500M for my own companies including a NASDAQ IPO. Overall, my direct angel portfolio is up 6x while my venture portfolio is only up 2x. After extensive analysis of my decision process versus returns, the key to superior angel returns became clear: The ability to separate weak investment signals from excessive noise in the very early stage incomplete information environment. My angel returns have outperformed by taking calculated early risk on non-obvious ideas with very weak traditional investment signals. As information becomes more complete and the investment signal grows stronger and obvious, returns go down: see Venture Capital returns. The only way to outperform is to be right about an idea which is non-obvious at the time you invested.

Over 10,000 start-ups in the US received their first outside funding last year. Each one thinks they will change the world and be a unicorn. They all have a story, some customer traction and some investors who believe in them. That is a lot of noise. I want to make 5-7 material angel investments a year with a high degree of confidence for a 10x+ return. Hoping to improve on my own, proven filter, I recently turned to Syndicates.

Angel syndication has grown for many good reasons. Syndicates typically invest in VC quality deals, often alongside VCs, with half the fees of a venture fund. There are software platforms that have significantly reduced the friction to create and manage syndicates as well as crowdfunding. While the smallest direct Angel investment check is usually $25,000, syndicate minimums can be as low as $1,000. Investors make a deal by deal decision rather than a fixed capital commitment. Investors often get access to deals they otherwise would not see at their local angel group, or through their limited friend network. Syndication has exploded lately, there are over 3,000 syndicates on Angellist alone. I was quite hopeful that Syndicates would be an effective filter layer to improve my Angel Investments. Unfortunately, this has not been my experience.

An explosion of Syndicates has created new problems for the Angel investor: Which Syndicates are any good? Does the lead add value that outweighs the cost of the carry? Some of the frustrations I have found as a syndicate investor include:

An Opaque Filter. When separating signal from noise, the PROCESS, and CONTEXT of HOW THE FILTER WORKS are all important. Many deal memos I get from syndicate leads are little more than regurgitations of the pitch deck. Many times I will get 2-3 deals a week from a syndicate lead. Is it really possible to find 2-3 unicorns a week? Every syndicate lead lists the impressive places they have worked before and a handful of successful deals, but most are very light on HOW they screen deals for syndication. Many leads also present deals across various stages and markets without any consistent theme. I call these “Any Good Deal” leads. How do they judge “Good”? Why, as an LP, should I trust your judgment? The most significant value a syndicate lead can bring is to share how and why investors should pay attention to this particular deal. Why do they have a strong conviction that it will deliver superior returns? Can a lead really be an expert in all stages and all markets? Sadly this process and context are lacking in most syndicates.

Misaligned incentives.. One of the first things that struck me on the first syndicate deal I received through Angellist was that the lead was only investing $1,000 into a $300,000 allocation. Basically, a no-cost option on 20% carry on $299,000 of other people’s money. If the investment doubles, the lead makes $1K on their investment and $60K in carry. 60 times more in carry! When the rake is more than the risk capital, you are playing against the house, not WITH the other players. I understand how that is great for the lead. I don’t understand how that is great for the investor. Many platforms will also drive investors to your deal, making the incentive for the lead to throw up as many deals as possible while putting as little of their own capital at risk. In many ways, syndicate leads are incented to be a POROUS FILTER which I find weird. Angel investing should not be a casino where the house has no risk capital and always wins.

Momentum overweighted.. It is tempting to mistake deal momentum for deal quality. Nearly every syndicate mail I receive has one or more of these trigger phrases: “Oversubscribed”, “Last check-in”, “Famous investor X, Y, and Z investing”, “Growing 30% M/M”, “YC Batch X”, or my favorite, “I had to fight for the allocation”. Reading many syndicate deal memos you could get the impression that deal momentum is the only thing that matters. “Buy before Midnight tonight!” Paul Graham puts a very fine point on the dangers of overweighting fundraising momentum:

If you ask most syndicate leads for their returns, you will see they are very close to Venture Returns. Why? They overweight momentum and only invest after VCs. To outperform in Angel Investing, you must focus on primary signals. Management, product traction, market traction, CAC/LTV, customer reviews are primary signals. Momentum is a proxy signal. I have found that overweighting momentum is lazy investing and doesn’t end well. Theranos anyone?

I started Incisive Ventures to solve these problems. To be the upgraded Syndicate I wanted for myself and my friends. To be a truly value-added filter reducing the noise and improving the investment signal. Upgrading the syndicate is a long-term project for us at Incisive Ventures, and here are a few of the ways we have started the process.

A fine-grained, transparent, filter.. It is clear some filters work better than others. When the recent fires on the west coast kept most people coughing inside, I happily drove around in my Tesla X with Bio-Weapon Defense mode engaged. The key to a great filter is that it is fine-grained and built with data-driven, proven technologies. There are many different ways to design filters and even poorly designed filters will work some of the time (a broken clock is right twice a day). At Incisive Ventures, we have built ours through a detailed data-driven analysis of 25 years of angel investing and continue to improve it with every new investment. By focusing on primary investment signals which have been proven to correlate to superior returns in the very incomplete information environment of early-stage, we have consistently been able to deliver superior returns. Our model focuses on what characteristics Unicorns had BEFORE they were unicorns. During the Seed stage. We have shared parts of our process with LPs through our Meta Themes and Deal Funnel posts. Our filter has been designed for early-stage technology investing. For different markets and different stages, one would design a different filter. Our filter has been backtested and we show you our work in every deal memo. Incisive Ventures is a low volume, high conviction syndicate. While not a guarantee of future returns, we put our money where our confidence is which leads us to…

Aligned incentives.. At IV, we are investors first, syndicate managers second. I put a significant PERSONAL check into every syndicate deal. With this commitment, our LP investors are truly investing WITH me, not handing over a free option on their hard-earned capital. While a few syndicate leads also follow this strategy, it is often from a FUND they manage and receive management fees on. Since they are paid to deploy the money, the bar for deploying it could be lower than for a personal check. I follow the same filter and deal memo process for every check I write. The Incisive Ventures syndicate is simply an extension of that process to share my work and get more money into deals I have a high degree of conviction on. Since the incremental work to syndicate is very low, I do not need to charge management fees to support the work. While VCs and syndicate rolling funds charge a management fee plus carry for the privilege of investing in every deal, through our Preferred LP program, we don’t charge management fees, reduce the carry, give you early access and guaranteed allocations in the hottest deals. You are not playing against the house at a Casino. We are truly investing together.

Execution focus.. Ideas are free. Execution IN THE CURRENT BUSINESS is the key to all early-stage startups. This is why Management carries a 50% weight in our filter. We dig past the prior successes, fancy companies and degrees, to understand how management is executing against the specific opportunity we are investing in. How personal is solving this problem to management? Is that passion shared across the management team? There has to be a compelling WHY that drives management? We test management resilience, war game market dynamics, pivots, competitive responses, dig into the company culture, and do reference checks. We dig into the primary signals that show how the company is executing against product development, market traction, and regulations (total 30% weight). External validation of execution like other smart investors, or celebrity endorsements are considered, but only as secondary, proxy signals after we have validated the primary signals. These tests for execution take time, another reason why we target 5-7 deals a year instead of dozens.

Unique pipeline.. There is definitely deal fatigue out there in the Angel community. Do I really want to see another YC company? If you do, there are syndicates who specialize in that. At Incisive Ventures, you are likely to see a unique stream of companies you will find nowhere else. Obvious problems have many people rushing to solve them. That is a red ocean. We like the Blue Oceans. Many of the companies that fit our Meta Themes are tackling non-obvious problems with proprietary technology in a unique way. We want to fund the leaders in a new fast-growing niche. In addition to the Venture firms, angels, and CEOS in my network, I always have a couple of personal theme areas that I am looking to fund the best company making a product that I want to buy. An example of this is my recent investments in companies bring Continuous Glucose Monitoring (CGM) from the diabetes market over into the general health and fitness market. I have worn a CGM for three years and tried every company in the space. I found the best ones and invested.

Curated, value added Angel Investors. Paul Graham has said that “Angel investors are the most critical.” and we tend to agree. Many angels have been founders themselves and have large networks to leverage. One of our IV Meta Themes is to only invest when we can be personally helpful to the company. Founders we talk to are increasing asking “Who is in your syndicate and how will they help us grow the business?” Many times, we receive an allocation because we delivered value BEFORE the company raised money. IV syndicate members were very active beta customers with in the CGM product space. When we approached the leader about financing, the CEO already had received value from our beta participation. Ability to deliver value over and above capital will become increasingly important for Syndicate leads. This is something Incisive Ventures is hyper focused on.

At Incisive Ventures, we have a high degree of confidence our companies ability to solve big, non-obvious problems at the time we invest. We know where to look by our Meta Themes. If we are right, our returns will outperform.

Angel investors should join syndicates to improve your reach and leverage your capital. Just make sure you understand and agree with the filter process and meta themes of the syndicate lead. Make sure the lead incentives are aligned with yours. We have a proven process to separate the investment signal from the noise. I have designed Incisive Ventures to be my dream syndicate. I hope you find yours.

For those investors who want to beat the crowds, today we are announcing our Preferred Limited Partner Program. Peter over at Unpopular Ventures runs a very good syndicate and I thank him for the inspiration of this syndicate upgrade.

In the past, in order to get access to all on thesis investments from a Venture Fund or a Syndicate Rolling Fund, investors are asked to pay management fees AND carry. This always seemed odd to me. As an investor, I make a long term capital commitment which helps the lead get into more deals, and you DOUBLE my fees? The lead is getting secure capital and I always thought investor fees should go down. Now, with the Incisive Ventures Preferred LP program, you get lower fees and many other benefits. Since I started the syndicate with a bunch of friends whom I have been investing with a long time, we have been piloting this since the beginning. We are now ready to consider new Preferred Limited Partners. Connect and let’s discuss.

Preferred Limited Partners commit to:

• Invest a minimum amount into every IV syndicate deal (minimum $5,000) over at least a 12 month period.
• Preferred LPs are able to opt out of any deal in which you have a personal or values based conflict, just drop me an email.
• IV is a low volume syndicated and we expect to do 5-7 deals a year.

What Preferred Limited Partners receive:

• No management fees
• Reduction of per deal carry to 15% on their investments.
• Early access to every deal (we will email you first)
• Guaranteed allocation of your Preferred LP commitment in every deal. No more getting cut back in oversubscribed deals.
• Preferred access to the Incisive Ventures team.

If you agree with our Meta Themes and how we filter the funnel, join my long time investing partners and put a portion of your angel investing allocation on auto-pilot. Become an Incisive Ventures Preferred LP. Let’s connect.

Incisive Ventures reserves the right to update terms and conditions for the Preferred Limited Partner program at any time. Current program terms here.

Over 8,000 companies received pre Series A funding in 2019. As I write, 2020 is on pace to surpass that. How does one separate the signal from the noise? Over 25 years of Angel Investing, I have made every mistake there is and built a process from all that learning. This is the process I use to select deals for the Incisive Ventures Angel List Syndicate. Here is how I do it.

The top of the funnel is not every possible deal, you must apply a filter. The first filter is my personal network built over decades as an LP in over a dozen Venture funds, Angel investor in over 100 companies, CEO having raised over $500M for my companies (and all those venture and banking relationships), Founder of the Angel network Element8, and all the management and investor relationships over that time. From that network, I see thousands of deals a year.

The second filter is the Meta Themes I have found deliver outsized returns when present. They are listed below. If you want to get into the weeds, there is a very detailed dive into it here.

• Software eats everything
• Great founders figure shit out
• Disruptive innovation creates new markets
• Platforms win
• Americans are lazy
• Invest only when I can be helpful
• Invest along other very smart, committed people.

After screening hundreds of deals through the Meta Themes, less than a hundred get the concentrated diligence process and end up with a weighted score. With every check I write of any size, I want to have a greater than 80% confidence in a 10x return on my capital. If you want to get into the weeds on the ranking algorithm, head over to this blog post. There are 5 major risk areas for every startup. I assign a confidence level from low (weak, unprepared, or insufficient) to high (easy, will crush it). The five components are:

• Management (50% weight)
• Product (10% weight)
• Market (10% weight)
• Regulation (10% weight)
• Terms (20% weight)

Less than a handful make it through to writing a check. My check size goes up along with my confidence interval. I usually write checks up to $50,000 between 80-90% confidence. Over 90% confidence, I will write checks up to $1M either alone or with friends and other smart investors. These are typically the deals that go through my Syndicate.

PS: Major Errors I have made.

While there is likely a whole post on errors I have made in the course of decades of Angel investing, the major ones that have cost me the most capital are listed here (in stack ranked order).

1. Weak management. Management that can’t execute and pivot over time. Most management have nice looking resumes, but until you dig deeper and understand how they execute and the kind of culture they create, you won’t understand if they are up to the startup challenge. Everyone has an idea. The winers out execute everyone else.
2. Underfunding. Most startups run out of money before they find a product/market fit. Many startups fundraise hand to mouth, never gaining enough capital to mitigate the big risks of the business. Underfunding can also be caused by overspending by management on the wrong problems at the wrong time (see above).
3. Big Market, unclear entry strategy. I have fallen in love with large market size numbers, we all do. Without a clear product path to enter the market with some sustainable advantage, the market size doesn’t matter. Without product/market fit, the size is irrelevant. Also, if the “market” is already big, there are likely lots of competitors, a red ocean. There are better returns creating a new market niche and leading that niche with your product.
4. Me to products. Never invest in a follower. Unless there is some geographic, language, or market reason. There has been a lot of money made copying innovation from the US in Europe for example. But copying a product in the same market tends to lead to low returns for investors. Invest in the leader, the category creator.
5. Following investors without personal theme fit. I started out Angel investing with an “any good deal” strategy. How did I decide if it was a “good deal”? If other “smart” investors were in it. You will never know why other investors write checks, or even if they are “smart”. Plenty of “smart” people put money into Theranos. They all lost their money playing the momentum of others without doing their own thinking.