RVI’s New Model 9 Months in: 2x members, more investments, more diversification

For 14 years I’ve led the River Valley Investors angel investor network. A year ago the group was on death’s door. Membership was down to the lowest levels since I’d taken over leadership from our founder and my mentor, Joseph Steig. And none of us knew that COVID was just around the corner. If RVI failed then our region would have lost its only active angel group – a huge potential blow to local startups.

It was time to pivot. I spent the last 3 months of 2019 conducting intensive customer discovery, interviewing RVI’s top members, past and present. They taught me a lot.

In January RVI leveraged that learning and pivoted to focus on speed, convenience, and syndicated deals. In March we switched to meeting online permanently.

The results:

  • Membership has nearly doubled in 9 months, pulling in people from a much larger geography than conceivable before.
  • Membership is continuing to grow at the fastest rate in seventeen years.
  • We’re investing in more deals than we’ve ever invested in before.
  • We’re helping our members get more diversification than they’ve ever had before.

I’m proud as hell of what we’ve done in less than a year, and excited to see where the next year takes us. We’ve accomplished all of these results because of the incredible feedback our members, past and present, generously gave in Q4 of 2019. I can’t thank them enough for helping ensure our region continues to have a source of high-risk capital for startups!

If you aren’t familiar with the River Valley Investors (RVI), we are a network of successful business executives and entrepreneurs who invest in exciting startups. No one investor has all of the time and expertise needed to fully vet all deals. That is why we only look at startups that have already passed the hurdle of securing another angel group or venture fund as their lead investor. RVI members then leverage each other’s expertise and networks to vet the opportunities and come to a decision in just a few short hours of work, then co-invest to secure optimal terms.

If that sounds like your cup of tea, learn what is required to be an RVI member.

The Quick and Easy Way to Find the Best Applicant From Among Hundreds

One of my favorite jokes goes something like this:

Whenever a new position opens up, and I have to sort through a stack of resumes, the first thing I do is take half of them at random and throw them away.

I don’t want unlucky people working in this department.

As with many good jokes, it’s funny because it has a nugget of truth to it.

Anyone who’s run an accelerator, a grant program, reviewed book/screenplay manuscripts, or been in charge of hiring has an impossible challenge: how do you find the proverbial needle in the haystack?

The answer is usually some variation on, “start sifting.”

Sorting through a massive pile of potential applicants is time consuming, boring, and feels pointless.

But we know that the results are undesirable. Being unable to fully and objectively review applicants perpetuates the existing weaknesses of the selecting culture, misses out on diamonds in the rough, and it is costly.

And it’s not like it’s a malicious problem – it’s just an effect of the system.

We just don’t have a better way to do it.

Or do we?

Option 1: Automate or outsourcing the task to less costly labor. Perhaps we give the young, inexperienced pre-screener a set of very simple rules of thumb like “Graduated from Harvard/MIT/Stanford” or “ready to work 40-hours-a-week on their venture.”

There are lots of problems with this. The first is that it inadvertently bakes in the flaws of our current systems as it prefers people who tend to graduate from top-tier schools or who can afford to work full time on their venture without going hungry or neglecting their family. You end up with a very young, white, and male demographic.

It also leaves out the ‘x-factor’. There are always factors beyond the obvious and quantitative that can signal a great applicant.

Option 2: Use Experienced Judges.

People who can spot that x-factor are rare, busy, and expensive. So we don’t use them until late in the process. When we do, we often use them in ways proven to be ineffective – for instance putting 3 judges in a room for 8 hours and sending applicant after applicant to them all day long. Studies show the applicants coming in at 5pm have a much lower chance of being accepted vs applicants coming in at 9am.

Another issue with these high-cost judges is that you often can’t get enough of them to achieve the diversity of perspective you need to spot the best applicants.


Because these people cost a lot of money, and moreover, are hard to find!

Oh, and on top of that, because of the cost of processing applications, there is NO practical way to provide feedback to the vast majority of people you reject. So, you can’t maintain a relationship with potential future applicants, nor give them a clear path to improvement.

How much of that applies to your system? What if you could do something better, more convenient, and at lower cost? Usually that requires a technological miracle. But in our case we just need to take advantage of a very old miracle – peer selection.

The Peer Selection Solution:

At Valley Venture Mentors (VVM) we created a selection process that improved on all of these issues – reduced cost, saved time, AND increased the quality of applications we accepted.

In short, it’s something of a miracle solution. And, like many miracles, we stumbled upon it largely by accident.

Let me show you how it works.

Step 1: Peer Selection

  1. The applicants submitted their applications, as normal. VVM’s applications, for example, had two sections:
    1. Pitch – Section describing the venture
    2. Rest – Everything else, notably: Entrepreneurs’ names, contact info, demographic data, etc.
  2. Drawing inspiration from research on blind auditions, we created packets containing 20 randomly selected Pitches without information about the founders. If you don’t know that the founder is female, of color, LGBTQ, etc. then that cannot influence your decision. (It isn’t perfect because if someone had a startup called “Black Girls Code” that information will be in the Pitch and the reviewer might make some educated guesses. However, we solve this later on in the process…)
  3. Give each applicant a packet and a limited amount of time to read, score, and provide feedback to every Pitch in their packet.
    1. Why 20? We wanted to have each company score as many of their peers as possible to get a more accurate score, but we had to balance that with the amount of time that would take the applicants to complete. Our goal was to have the whole process take < 4 hours so that the applicants wouldn’t get tired and start scoring people too harshly.
  4. This was all done with Google Forms and Google Sheets, so no costly or confusing software was required!
  5. We had a few simple checks to see if someone was gaming the system. We kept an eye out for things like:
    1. If you scored teams low that everyone else scored high (or vice versa).
    2. If you seemed to give random scores or score everyone the same.
    3. If you gave little or no feedback.
  6. Then we used some spiffy math to adjust for the fact that some people grade generously, some harshly, some with a tight spread, some use the whole scale, etc.
  7. We disqualified anyone who we felt was trying to game the system. In theory, this could be tricky. In practice, of the very few people who tried to game the system, 100% of them ended up with low scores from their peers anyway. I assume that would not always be the case, but it was the 3 years I managed the process.

Simultaneously we had a Control Group – a group of the usual kinds of people who are used as judges – the expensive people. We had them review a random packet and compared their scores to the crowd’s. The scores were 80% the same.

Benefits of Our Peer Selection System

  • Faster – Processed hundreds of applications in 1 week
  • Cheaper
    • Almost no “expensive” talent (just the 5 control group judges)
    • A small portion of time from two staff people
    • No expensive software!
  • Better
    • Dramatically reduced unconscious bias.
    • Every applicant received feedback from more than a dozen peers.
    • Tests the applicants’ commitment and willingness to work for the position (if they submit no peer review scores, you can safely disqualify them).
    • The activity, one of the first any entrepreneur would experience working with us, showed applicants how serious we were about being a community and living by our values. It helped us find our kind of entrepreneurs and let them know we were right for them. In short, it made them like us. A lot.

That’s how it worked. Knowing this, you can build one for your program. If you’d like help I can put you in touch with someone you could contract to help you. Reach out to me on LinkedIn

A Taxonomy of Customer Pains and Benefits

I’m sure you’ve seen this before.

A triangle with the three vertices labeled as follows: Premium, Convenient, Cheap
positioning triangle

This triangle is a super-simplified way of discerning what pains your product or service is solving. In short, it helps you discern your value proposition.

Your company’s value proposition must provide benefits that perfectly match your customers’ pains. If the customer has no cash, you’ve got to be cheap. If they have no time, you’ve got to be fast, and so on.

First-time entrepreneurs asked to document their hypotheses about Pains and Benefits often experience “blank canvas” paralysis, the inability to get going because of a lack of a clear starting point.

That’s where this handy triangle comes in. It gives you a brief list of options, from which you can choose what fits best with your company and your customers.

This is very imprecise though.

It’s never as simple as, “I don’t have any cash,” or, “I’m short on time.”

If you want to solve the customer’s pains, you’ve got to understand them on a deeper level.

Of course, this requires interviewing your customers at length to get a full picture of the problem they are facing.

But, there is an intermediary step you can take.

This blog post aims to provide a set of categories and examples to guide an entrepreneur to find the relevant pain hypotheses, which can then be tested in interviews.

Each heading lists a category of Pain/Benefit. This is not an exhaustive list. Deep knowledge of your stakeholders will provide far more specific pain points and benefits. However, this list can kickstart the exploration process by giving you a running start.

So, find the pains that you think your customers may be feeling, then go out and talk to them about it!

Existential Risk / Survival

Losing their jobSaving their position
Ruining their careerMaintaining their career
BankruptcyFinancial stability
Physical painFree of discomfort
DyingLive long & prosper

Money (too little / more)

Expenses too highA growing savings account
Revenue too lowMore customers
More revenue from existing customers

Time / Convenience

Too many tasks to do every dayA simpler schedule
No personal timeMore personal time
Deadline missedHit the deadline with confidence

Shame / Status

Fear Of Missing Out (FOMO)Pride in being in the “in” group
Failure leads to public shame
Fear of being mediocre
Status increased
Impact recognized

Lonely / Connected

Depressed by lonelinessJoy from belonging
Socially isolated
Can’t find their “tribe”
Can’t breakin to social network
Connected to a community of like-minded people.

Bored / Fun

Ignorant of a topic of interestMastery of their craft
Seen it all beforeNovelty, something new to experience

The KISS Scorecard Helps Founders, Investors, and Mentors Focus on What Matters


Entrepreneurs and investors used to rely on strictly qualitative/gut methods of assessing progress and deciding what their next steps should be.

In 2014 the great Steve Blank gave the startup world its first widely-respected quantitative assessment system: the Investment Readiness Level (IRL). A few years later Village Capital took the IRL to the next level, creating the Venture Investment and ReAdiness Level (VIRAL). It took Steve’s IRL and essentially added a second dimension, a set of 8 milestones for each IRL level. It is a fantastic tool to help highly scalable startups understand where they are at in terms of being ready to raise venture capital funding.

VIRAL is an excellent tool used by many. However, it didn’t work for my students. It puts nearly equal weight to all components of a business at every level of its development, whereas I find that in the early days almost all your attention should be on customer discovery, and later on it should be about product development, then on marketing, and so on. Also, while my students are building scalable businesses, few are building venture capital scale businesses, and many of the milestones in VIRAL weren’t quite right for us.

In a Nutshell

And so was born the KISS (Keep It Super Simple) Scorecard. At its most basic, it is a way to let a startup CEO/investor/mentor know what they should be focusing on, and it does so by helping them tell a story…

  • Level 1: Idea – A founding team with passion and an idea to solve a large, important problem.
  • Level 2: Market – Identified a viable market of customers who’s “hair is on fire.
  • Level 3: Value Proposition – Initial product that customers are thrilled with and is superior to the competition.
  • Level 4: Relationship – Cost-effective methods to Find, Get & Keep customers.
  • Level 5: Financials – Revenue model, cost structure, and unit economics are proven and profitable.
  • Levels 6+: Scale 10x – Grown 10x, fixed what broke along the way, and remain profitable.

The Milestones

Like VIRAL, the KISS Scorecard has milestones for each level but more than half are on the specific aspect of the business it should most be focusing on. So for companies in Level 2: Market, most of the milestones have to do with understanding your market/customer discovery. For companies in Level 4: Relationship, most of the milestones are on finding cost effective marketing, sales, and retention strategies. Each level also has dedicated milestones for the few things startups always need to pay close attention to: Team and Fundraising

Also like VIRAL, KISS Scorecard’s right-hand side depicts what flavors of capital tend to be the best fit for companies given their level. Let’s take a look (click to enlarge).

KISS Scorecard

How to Use the KISS Scorecard

  1. Get your own (free!) digital copy of the KISS Scorecard. If you like paper, go to the “print” tab and you can cross off milestones as you go. From here on out though we’ll assume you are using the “Digital” tab.
  2. Mark your current status. Go through the Scorecard and mark off each milestone you have completed. To do so just put an “a” in the tall, skinny cell to the left of each completed milestone. When you do so, you’ll notice the milestone will get a black background and the text will turn white. Your score (in the upper left corner of the document) will increase. Your score goes up by 1/9 for each completed milestone. Note that all the milestones are in columns D onwards, columns A-C should not be edited as they are labels, not milestones. Next go to the Log tab and in the row associated with the “a” assessment, put today’s date.
  3. Find your gaps & set your priorities. As the leader of a company one of your top jobs is to determine what few tasks of the infinite pile are the priority. The lowest-level uncompleted milestones on your Scorecard should generally be your top priority. If they aren’t, you should make sure you have a good reason.
  4. Repeat. Periodically (probably every 1-3 months) you should update your Scorecard and use it to guide your medium-term goal setting. Use a new letter for each assessment (“b” for the second, “c” for the third, and so on), leaving your old letters in place. Doing so gives you a grayscale bar graph showing the evolution of your startup over time. Be sure to update the “Log” tab each time so you have the dates of each assessment recorded. This is a great activity to do with your board of advisors. Asking them to “bless” you marking milestones as complete (even in a non-binding way) can create accountability most of us need.


Let’s walk through a fictitious example (picture of it below as well)

Example KISS Scorecard

We can see the evolution of Magic Mops’ progress over time on this scorecard. The black cells with white text show them as they entered an accelerator with little more than idea (the “a” assessment). The progressively lighter gray “b” and “c” assessments followed each month thereafter as they applied what they learned in the accelerator. We can see they didn’t think much about fundraising until the end of the accelerator and otherwise were mostly adding one layer of knowledge at a time. Then, after graduation, they go to autopilot.

Fast forward a year. Magic Mops’s product was in the market and generating a few hundred thousand dollars in revenue. Wahoo! The CEO was spending most of her time on ramping up sales & marketing efforts. She runs into her old KISS Scorecard from the accelerator and realizes she hasn’t updated it in all this time. At her next board meeting she asks everyone to help update the scorecard. The conversation is illuminating.

First of all, her score is listed as 3.0, not the level 5 or 6 she expected given the her recent sales successes. This gives her and the board pause. So she looks more closely…

Yes, she has 1 milestone in level 6 and one in level 5 crossed off. A few bigger customers took a chance on her, so she felt pretty confident. But, there is a huge problem. She’s spending time on high level milestones when the very foundation that work is built upon is unsound. Critically, she is missing:

  • Milestone [2.4] “Our initial target customers love the product, pay for it, and keep using it” – People have ordered, but there have not yet been any reorders.
  • Milestone [2.5] “Customers validated our solution is superior to competition” – While the janitorial staff using the mops love them, there is zero evidence from the paying customers that the product is superior for them.
  • And all the Level 4 milestones are incomplete. Many things have been tried, some successes came in, but nothing that is scalable or repeatable or even consistently measureable.

Scaling up right now would be begging for the #1 cause of startup death, premature scaling. Instead, she needs to put almost all of her attention into milestones 2.4 and 2.5. Only after she has proof that those milestones are completed can she start working on sales & marketing with confidence. Her board helped her reorganize her strategy and ToDo lists to focus obsessively on these milestones.

She just dodged a company-killing mistake.

Hopefully, so can you.

Get your KISS scorecard (for free!) now.

A Canvas That Tells a Story: KISS Canvas (v3.1)

[This is part of a series on the KISS Canvas]


30-page business plans are great for established businesses and terrible for startups that need to iterate quickly. 15 years ago the Business Model Canvas (BMC) changed everything by giving us a 1-pager (or 4×3 foot poster) to help you quickly document and test the key hypothesis behind your business model. The BMC was a quantum leap forward.

However, my students and I often struggled with the structure of the canvas. While it was superior to a business plan it was relatively hard to read & use. You literally needed a map to show you how to read it – start here, jump to there, then jump down to here…

In a Nutshell

And so was born the KISS (Keep It Super Simple) Canvas. Each key stakeholder (payers, users, channel partners, etc.) gets their own row. Read the columns in each row from left to right and you’ll find the facts of the business model layed out in a logical narrative structure. In fact, it tells the story of your business, as you would in a good pitch. The bottom of the canvas holds the “waterfall of wisdom” where you store your invalidated hypothesis, so you can easily remember and tell the story of what you’ve learned in your startup journey. No map required.

At the highest level, this KISS canvas tells the following story just by reading from left to right: We help [key Stakeholders] by providing [value proposition]. We find, earn, and retain their trust by [relationships]. This is economically sustainable because of [financials].


We help the blind and visually impaired by empowering them to connect with their fully sighted friends and family as equals. We find, earn, and retain their trust through word-of-mouth and strategic partnerships with nonprofits that serve the blind. Customers pay us an $8 monthly subscription.

And today, after 3 years of field testing, I’m proud to roll out version 3! It has two variants. The first is…

KISS Canvas (Lite)

This variant is for people at the “I have an idea” stage.

KISS Canvas (Lite)
  • Key Stakeholders – Who do you serve?
    • Segments – Name each of the groups of people you will deliver value to: payers, users, channel partners, etc. Each gets their own row.
    • Deciders – Describe the actual people (COO, front-line employee, Head of New Products, etc.) who make the decisions for each segment.
    • Pains – What problems do they have?
  • Value Proposition – What do you offer?
    • FeaturesHow will you solve their problems?
    • Benefits – What promises are you making to your customers?
    • Competitors – Who else is solving the problem?
    • Competitive Advantages – How are you superior at solving the problem?
  • Relationships – What kind of relationships will you have with each segment?
    • Marketing – How will you make people aware of your solution?
    • Sales – Once aware of you, what process will they go through to use/pay for your solution?
    • Retention – Once someone is using your solution, how will you retain their loyalty?
  • Financials – How does the money (and value) flow?
    • Value Model – What value does each segment provide you in return for your product (money, attention, referrals, etc.)?
    • Pricing – How much do you charge?
    • Cost Structure –  What are the costs associated with running your venture?
  • Waterfall of Wisdom – When you disprove a hypothesis, have it “fall” vertically down into the Waterfall of Wisdom. Each hypothesis in the waterfall represents something you thought was true… and found out it was not! That’s the beginning of wisdom :).

KISS Canvas (Full)

If you are past the I-have-an-idea stage and ready to really develop your business model, then you’ll need to start answering much more detailed questions in each section. If that is you, then check out the full version of the KISS Canvas, where just about all the top-priority questions for a startup have been laid out in step-by-step, fill-in-the-blank fashion…

KISS Canvas (Full)

Examples (inspired by real startups):

Get Your Own (free!)

If you would like to use the KISS Canvas, you may do so completely for free as they are licensed under creative commons :).

Check out more KISS Canvas Content.

How to Come up With Great Ideas

Hand holding light bulb and cog inside. Idea and imagination. Creative and inspiration. Innovation gears icon with network connection on metal texture background. Innovative technology in science and industrial conceptIf your startup/organization/team struggles with ideation (the process of coming up with ideas), you fall into one of two camps:

  1. Those who struggle to come up with any ideas.
  2. Those who come up with plenty of ideas but struggle to identify which ones are worth pursuing.

What follows is a step-by-step guide for solving both problems.

The Short Version

  • Step 1: Get MAD – Remember your Mission, assess your Assets, document the Demand.
  • Step 2: Ideate – Use your MAD to inspire ideas.
  • Step 3: Select Criteria – Determine what is important to your decision-making process.
  • Step 4: Score – Score each of your ideas based on the criteria.
  • Step 5: Decide –  Review the results, make sure your scores are correct, and determine which idea(s) are the highest priority to pursue.

The Details

At the heart of the solution is a simple canvas-style tool: The MAD Ideation Canvas. Like other “canvases” (such as the KISS Canvas or Business Model Canvas), this canvas replaces big, complex ideation systems with a fast, fun, and easy-to-iterate tool. Nothing fancier than a pen, open-mind and sticky notes required!

Here is what the 4×3 foot poster looks like:

MAD Ideation Canvas Template - Poster_ 4 x 3 feet

Download & print the 4×3 ft poster, grab some sticky notes, and follow along. If you prefer to do things on a computer then use our digital version. If you don’t the canvas format then try our worksheet version.

Let’s get started, and as we do, we’ll fill in the canvas with an example from the fictitious Montessori School of MyTown.

Step 1: Get MAD

The best ideas resonate with your personal/corporate/organizational Mission, leverage your Assets, and meet Demand from customers/clients/stakeholders. MAD for short.

IdeaJam-MAD Venn Diagram

  1. M: Remember your Mission – This what drives, motivates, and guides you.
    1. Your first sticky note should contain the essence of your mission boiled down to 8 or fewer words.
      1. Empower children to be great global citizens
    2. Fill the remaining space with stickies that further illuminate your mission and/or values.
      1. Follow the child
      2. Peace
      3. Parent partnership
      4. Joyful environmentMAD - M
  2. A: Assess your Assets – Assets are resources you could put to work right away.
    1. Superpower – Your first post-it should be your superpower. Is there something you are one of the best in your part of the country at (or the whole country, or the world)?
      1. Anti-racism and inclusion curriculum this school’s curriculum is the subject of talks at national conferences.
    2. Physical assets that are not used 100% of the time such as: classrooms, labs, dorms, special equipment.
      1. Classrooms
      2. Playground
      3. Reusable classroom materials
    3. People who are awesome but only working part-time or who are not being used to their full potential.
      1. Teachers
      2. Staff
      3. Board members
    4. Relationships with people such as: customers, volunteers, alumni, other organizations/companies, government agencies, your community.
      1. Other independent school leaders
      2. Alumni
      3. Families of students/alumni
    5. Gravitas earned from places such as: media coverage, awards, reputation for great work.
      1. Multiple awards
      2. Speaker at national conferences
    6. Know-How your team has developed to solve your own problems such as: processes, curriculum, understanding of complex systems.
      1. Anti-racism and inclusion curriculum
      2. Nature curriculum
      3. Financial aid system
      4. Comfort w/ technologyMAD - A
  3. D: Document the Demand – List out any loud signals the market or your customers have given you of things they want.
    1. What have they been asking you for and you’ve said NO to? A subset of this can be something you offer and there is a waiting list to get in, or a long line, you are turning people away because there isn’t enough room, etc.
      1. Montessori for families to use at home
      2. More extensive after-school programming
      3. Year-round programming
      4. Keep asking us to speak at conferences
      5. Teachers elsewhere asking for our techniques
    2. What are similar orgs offering that you are not?
      1. Renting out their space to people who run classes in the evenings
      2. Running child-friendly co-working spaces
      3. Selling curriculum to other schoolsMAD - D

Step 2: Ideate – Use your MAD to inspire ideas

So the whole MAD part of the canvas looks like…

MAD only

  1. Generate – Take five minutes to have each person on your ideation team privately & silently write down a list of ideas inspired by your MAD.
  2. Share – Have each team member read off their list. Create sticky-notes for each idea and add them to the Idea row on the canvas (the row that goes Idea 1, Idea 2, Idea 3…). Make sure to ask each other questions to be sure you understand each idea. Add any new ideas that are generated by the dialog.
  3. Simplify
    1. Combine ideas that are similar.
    2. Split up compound ideas.
    3. Some ideas were unclear. Rewrite their names/descriptions so everyone “gets” what the idea is about.
    4. If there are more than 14 ideas, the team leader should select which ideas go on the canvas today.
      1. Montessori @ home – Montessori kids cook for themselves, clean up their messes, and are kind & courteous. Not so much at home. Parents could hire the school to teach them how to have the Montessori behaviors come home :).
      2. Premium after-school – Current offerings are thrown together at the last minute and are basically glorified babysitting. What if we offered ultra high-quality programming parents would be willing to pay extra for and that might attract people from other schools?
      3. Year-round programming – Make it possible for kids to continue their standard Montessori education over the summer (vs going to summer camps). 
      4. Renting out space – Rent our classroom space (after hours) to consultants, yoga instructors, etc.
      5. Child-friendly co-working – Dedicate one of the empty rooms in our new building to be dedicated co-working space. Good for parents of current students and might attract new parents to the school.
      6. Teach teachers anti-racism curriculum (online) – Teachers/schools pay to become trained and certified in our curriculum. All done online so we can access people anywhere in the country.
      7. Nature curriculum teaching retreat – Similar to the previous idea, although as it would be nature-based the training would have to be in-person.
      8. Financial aid webinars for other schools – They pay to attend webinars run by our CFO.

Step 3: Select Criteria – Determine what is important to your decision-making process

Most people’s process for debating ideas ends up being “whoever makes the best argument.” This sounds meritocratic, but it really isn’t.

  • Sometimes people with bad ideas win the argument because they are great at arguing.
  • Sometimes people with great ideas lose the argument because they lack sufficient rhetorical skills.

That’s not how to make a decision. You want to make decisions based on good data. One way to get good data is to agree on the criteria by which the ideas will be evaluated. Then score the ideas and look at the how the numbers fall out.

  1. Generate – Take five minutes to have each person on your ideation team privately & silently write down a list of criteria important to them.
  2. Share – Have each team member read off their list. Create sticky-notes for each idea and add them to the Criteria column on the canvas (the column that goes Mission alignment, …, Criteria 5, Criteria 6, Criteria 7). Make sure to ask each other questions to be sure you understand each criteria.
  3. Simplify
    1. Combine duplicate criteria.
    2. Clarify criteria so everyone “gets” them.
    3. Each criteria should be worded so that high scores are Good Things for your organization. Example: if you want to make sure that ideas are not expensive, your criteria should be “Inexpensive.” If you are afraid of ideas that could hurt your reputation, the criteria should be “Good for Reputation.” For our fictitious Montessori school the list starts with the standard four and then adds some (bolded):
      1. Mission Alignment
      2. Have the assets
      3. Proof of demand
      4. Revenue potential
      5. Fast & Cheap to try
      6. Help us recruit more students
      7. <No 7th criteria selected>
  4. Weight – Some criteria are more important than others. Let’s select some criteria to be weighted twice as heavily in the final calculations.
    1. Generate – Each team member should privately & silently take 60 seconds to write down the 2 criteria they think are the most important.
    2. Share – Everyone shares.
    3. Decide – The team leader decides which criteria (no more than half the criteria, please) are the most important and puts a star to the left of the criteria title. For those doing this on the digital canvas, put an * in column A just to the left of the selected criteria.
      1. The Montessori School puts stars on criteria 4, 5, and 6

Step 4: Score – Score each of your ideas based on the criteria

  1. Generate – Each team member should privately & silently score each idea on each criteria. We generally recommend a scale of 0-2 with 0=this idea does not (or basically does not) meet this criteria; 1=this idea meets the criteria so-so; 2=this idea totally meets this criteria. You can do this by giving each team member their own unique set of colored sticker-dots (so later everyone can easily see who gave each score). Everyone will see each others’ scores, but we recommend you instruct people to ignore what their peers are doing at this stage.
  2. Sum – Once everyone has placed their stickers someone needs to sum up how many dots are in each idea’s column, remembering to count starred criteria twice. The sum goes in the bottom row. Those using the digital canvas don’t need to do this manually as it calculates it all for you.
  3. Highlight – Circle the 2-4 highest-scoring ideas. If you are using the digital version of the canvas, it should automatically color code the scores. Red=lowest scores, Green=highest scores.

It should look something like this…

Montessori scoring example

If that is hard to read, check out the google sheet the image came from.

Step 5: Decide –  Review the results, make sure your scores are correct, and determine which idea(s) are the highest priority to pursue

  1. Double-check your math so you avoid making decisions based on bad data!
  2. Where there any surprises? Did any ideas people thought were great/bad end up scoring the opposite? If so, is that because the wrong criteria were selected, there was miscommunication about the idea, or because people’s initial gut feeling was wrong? All of those are valuable things to learn!
  3. Engage in a lively team discussion about the top-scoring ideas. Focus the conversation around criteria where there was a lot of disagreement in scores. This is a chance to learn from your teammates’ perspectives. People may volunteer (don’t ask them to do it) to change their scores.
  4. Review the finalized numbers.
  5. The team leader uses these numbers as a guide to determine which idea(s) they want to prioritize, and to do so with confidence. In our example Montessori school, the Head Of School decides to invest resources in further exploring the top 3 scoring ideas and one that her gut says to explore more:
    1. Premium after-school
    2. Teach teachers anti-racism curriculum (online)
    3. Year-round programming
    4. Child-friendly co-working space



Startup Pitching Checklist

This is the checklist/boil down of the techniques listed in the prior 3 posts in the “Startup Pitching” series. After you complete a draft of your pitch, go over this list to make sure you’ve applied as many of the techniques as possible. If you want any of the checklist items expanded just click on the section header (Beginner, Intermediate, Advanced) to go to the blog post that explains the details.

  1. Beginner (101)
    1. One rehearsed presenter – Pick one person to deliver your presentation, don’t tag-team your pitches.
    2. Know your audience – Customize everything about your pitch to meet the cultural norms of your target audience.
    3. Set your objective – Your objective is to get another date, not marriage/investment. Stop freaking out :).
    4. No jargon or acronyms – Use plain English accessible to a lay audience.
    5. Split up your slides – Turn a slide with X bullets into X slides with one bullet each.
    6. Make fonts readable – Minimum of 30 points. Period.
    7. No Math – Don’t show any derivations, just show the results.
  2. Intermediate (201)
    1. Dead seagulls – Put a large, immediately relevant image on almost every slide.
    2. Front load credibility – Put the 1-3 most credibility-establishing facts about your company right after your title slide.
    3. Plant seeds, don’t tell it all – You don’t have time to tell it all, so boil down each section of your business to the 1-3 most important parts.
    4. No BS Financials – Focus your financials on fundamental economic drivers of your business, not BS projections.
    5. The one number rule – Don’t have more than one number (maybe two) on a slide.
    6. Use relative values – Don’t give absolute values, instead convert them into relative values.
    7. Prep for Q&A – Before your pitch identify the most likely questions and have polished answers ready to go.
  3. Advanced (301)
    1. Timing is everything – Make sure that on the slides immediately before powerful images your speech prepares the audience.
    2. Tell a story – Don’t rattle off facts, weave them into a story.
    3. Inoculate the audience – Address any deal-killing objections right in your presentation. Don’t wait for Q&A.
    4. No complex issues – If there are any complex issues in your business that you know are not relevant, don’t bring them up on the 1st date.
    5. Results not resumes – Identify the 2-4 most critical skill sets a company like yours needs and then show examples of your team doing exactly those things… brilliantly.
    6. Risk reduction, not line items – Don’t tell us what things you are spending money on, tell us what risks you will mitigate.

Hungry for more? Here are 25 more tips from some of the top people in the angel investing world.

View all posts in the “Startup Pitching” series

Startup Pitching 301

This is the 3rd post in the “Startup Pitching” series. In this post, we’ll go over advanced-level (301) techniques.

1. Timing is everything

Once you get good at using Dead Seagulls on your slides you want to take a page out of the comedian playbook… dramatic timing. If the image on a slide is particularly powerful, you don’t want to bring the slide up and then explain it. That will confuse the audience or rob you of the emotional punch you could have achieved. Instead, prepare the audience during the prior slide and then advance when the emotional timing is right.

2. Tell a story

At least a hundred thousand years before science and logic were developed we humans communicated via stories. Our brains are hard-wired to digest information packaged that way. Stories center on people, not bullet points. They have a protagonist and often an antagonist. So take your facts and craft a narrative around them.

You might start with a set of facts like this…

Our website allows customers to find and play games with friends, family, and strangers. Like a play-by-play on the radio, our game reads aloud all of the action and text chat.

And turn it into something more like…

Jane invites her grandson to join her in a game of cards on our site. Minutes later they, and several others, are playing and chatting. No one can tell who is blind and who is sighted… they only know who is winning – Jane! 

And don’t just do it on one slide. Your protagonist should keep appearing in your story. Weave the narrative through as much of your presentation as possible. Here are some more advanced tips for adding narrative to your pitch.

3. Inoculate the audience

Most vaccines work by giving a person a weakened version of a virus/bacteria before they would normally encounter it. You can take the same concept and apply it to your pitch. If there is a certain kind of objection that comes up again and again during Q&A, that is a signal you need to address it right in your presentation.

For example, my first company made video games for the blind. It turns out that most investors thought that all blind people were also intellectually disabled. Once we realized this, we updated our pitch so that our narrative featured Jane (mentioned above) who clearly was not intellectually disabled. We made sure to introduce our blind teammate  wrote code and skied.

4. No complex issues

Continuing our dating example… imagine this situation. You are going on your 1st date with someone and, for completely legitimate reasons, your X is currently living with you. If you bring this up on the first date, is there a second date?

Heck no.

Why? Because there isn’t enough time and trust to go over something complex like that. The purpose of the first date is to get a basic understanding and decide if a second date is warranted.

So if there are any complex issues in your business that you know are not relevant*, don’t bring them up on the 1st date. They should be brought up when you have the time and trust to explain things fully. Often times company financials fall into this category as they are just too complex to go over in spreadsheet form at a pitch meeting.

* You’ll notice in the example I gave the X was living with you for legitimate reasons. If they were living with you because you two are friends with benefits… that seems like a legitimate deal-breaker for the person you are going on a first date with!

5. Results not resumes

This is a specific application of the Show, don’t tell rule. The team section is one of the most important (arguable the most important) part of your presentation. Almost everyone does it the same way, by telling the audience about the resumes of their team members. This is dumping data on the audience and asking them to connect the dots. Also, resumes tend to emphasize the wrong facts.

As you want their funding/support, don’t make the audience work that hard! Spell out for people why your team is right for your venture.

In general, you should ditch the names, titles, degrees, and previous employer info. Instead, identify the 2-4 most critical skill sets a company like yours needs and then show examples of your team doing exactly those things… brilliantly.

The ideal team slide sounds something like this:

[for a company making artificial-intelligence software for hospitals]

From what I’ve told you so far, I bet you can see a few critical skill sets our team needs.

  • The particular kind of artificial intelligence needed for this work is very rare. There are only about 1000 people in the world qualified to do it. We have five of them.
  • Selling software to hospitals is notoriously difficult. Fortunately for us, previous to founding our company our CEO sold $100 million worth of software to hospitals.

The presenter narrowed it down to the 2 most important skill sets for a company like theirs and then showed how their team has a track record that should put funders’ minds at ease.

6. Risk reduction, not line items

Entrepreneurs tend to explain to funders how they will spend money. Often in a graph that looks something like this…

How we will burn your money

This seems logical but it sends the wrong message. As a mentor once told me…

“Don’t tell me how much of my money you will burn. Tell me what amazing accomplishments my money will allow.”

A startup is a bundle of risks. Its valuation goes up as it mitigates those risks. So don’t tell us what things you are spending money on, tell us what risks you will mitigate.

Bad example: “This round of financing will be used primarily on working capital to keep us alive until we’re ready for the next stage.”

No one (except maybe your mother) cares about keeping your company alive :(.

Good example: “This round of financing allows us to get a commercial grade prototype into the hands of key influencers in our target market.”

This shows the funders that you A) know what your next major milestone is and B) this money will let you hit it. Staying alive to do so is understood :).

View the startup pitching checklist | View all posts in the “Startup Pitching” series