I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

It's ok and even desired to be unprofitable if you're gaining revenue at a reasonable cost and have 100%+ net dollar retention, meaning you never lose customers and expand them. To estimate the acceptable cost of new SaaS revenue, we compare new revenue to operating loss and payback period. If you pay back the customer acquisition cost in 1.5 years and never lose them (100%+ NDR), you're doing well.

To evaluate payback period, we compared new revenue to net operating loss for the last 73 SaaS companies to IPO since October 2017. (55 out of 73). Here's the data. 1/(new revenue/operating loss) equals payback period. New revenue/operating loss equals cost of new revenue.

Payback averages a year. 55 SaaS companies that weren't profitable at IPO got a 1-year payback. Outstanding. If you pay for a customer in a year and never lose them (100%+ NDR), you're establishing a valuable business. The average was 1.3 years, which is within the 1.5-year range.

New revenue costs $0.96 on average. These SaaS companies lost $0.96 every $1 of new revenue last year. Again, impressive. Average new revenue per operating loss was $1.59.

Loss-in-operations definition. Operating loss revenue COGS S&M R&D G&A (technical point: be sure to use the absolute value of operating loss). It's wrong to only consider S&M costs and ignore other business costs. Operating loss and new revenue are measured over one year to eliminate seasonality.

Operating losses are desirable if you never lose a customer and have a quick payback period, especially when SaaS enterprises are valued on ARR. The payback period should be under 1.5 years, the cost of new income < $1, and net dollar retention 100%.

I've worked in a People role at seven early-stage firms for over 15 years (I enjoy chasing a dream!). Few of the seven achieved profitability, including unicorn status or acquisition.

Did early-stage startups share anything? Was there a difference between winners and losers? YES.

I support founders and entrepreneurs building financially sustainable enterprises with a compelling cause. This isn't something everyone would do. A company's success demands more than guts. Founders drive startup success.

Six Qualities of Successful Startups

Successful startup founders either innately grasped the correlation between strong team engagement and a well-executed business model, or they knew how to ask and listen to others (executive coaches, other company leaders, the team itself) to learn about it.

Successful startups:

1. Co-founders agreed and got along personally.

Multi-founder startups are common. When co-founders agree on strategic decisions and are buddies, there's less friction and politics at work.

As a co-founder, ask your team if you're aligned. They'll explain.

I've seen C-level leaders harbor personal resentments over disagreements. A co-departure founder's caused volatile leadership and work disruptions that the team struggled to manage during and after.

2. Team stayed.

Successful startups have low turnover. Nobody is leaving. There may be a termination for performance, but other team members will have observed the issues and agreed with the decision.

You don't want organizational turnover of 30%+, with leaders citing performance issues but the team not believing them. This breeds suspicion.

Something is wrong if many employees leave voluntarily or involuntarily. You may hear about lack of empowerment, support, or toxic leadership in exit interviews and from the existing team. Intellectual capital loss and resource instability harm success.

3. Team momentum.

A successful startup's team is excited about its progress. Consistently achieving goals and having trackable performance metrics. Some describe this period of productivity as magical, with great talents joining the team and the right people in the right places. Increasing momentum.

I've also seen short-sighted decisions where only some departments, like sales and engineering, had goals. Lack of a unified goals system created silos and miscommunication. Some employees felt apathetic because they didn't know how they contributed to team goals.

4. Employees advanced in their careers.

Even if you haven't created career pathing or professional development programs, early-stage employees will grow and move into next-level roles. If you hire more experienced talent and leaders, expect them to mentor existing team members. Growing companies need good performers.

New talent shouldn't replace and discard existing talent. This creates animosity and makes existing employees feel unappreciated for their early contributions to the company.

5. The company lived its values.

Culture and identity are built on lived values. A company's values affect hiring, performance management, rewards, and other processes. Identify, practice, and believe in company values. Starting with team values instead of management or consultants helps achieve this. When a company's words and actions match, it builds trust.

When company values are beautifully displayed on a wall but few employees understand them, the opposite is true. If an employee can't name the company values, they're useless.

6. Communication was clear.

When necessary information is shared with the team, they feel included, trusted, and like owners. Transparency means employees have the needed information to do their jobs. Disclosure builds trust. The founders answer employees' questions honestly.

Information accessibility decreases office politics. Without transparency, even basic information is guarded and many decisions are made in secret. I've seen founders who don't share financial, board meeting, or compensation and equity information. The founders' lack of trust in the team wasn't surprising, so it was reciprocated.

The Choices

Finally. All six of the above traits (leadership alignment, minimal turnover, momentum, professional advancement, values, and transparency) were high in the profitable startups I've worked at, including unicorn status or acquisition.

I've seen these as the most common and constant signals of startup success or failure.

These characteristics are the product of founders' choices. These decisions lead to increased team engagement and business execution.

Here's something to consider for startup employees and want-to-bes. 90% of startups fail, despite the allure of building something new and gaining ownership. With the emotional and time investment in startup formation, look for startups with these traits to reduce your risk.

Both you and the startup will thrive in these workplaces.

OpenAI's ChatGPT is an amazing AI-powered chatbot. It can write poetry, stories, and marketing campaigns, and it's also adept at coding. ChatGPT's coding is so amazing that it replicated itself. What happened:

Me: Hi

Hello! Can I help? I'll answer any inquiries you have.

Me: Build a python and flask AI chatbot that responds to user messages on the frontend.

CGPT:

from flask import Flask, request, jsonify

import openai
openai.api_key = "YOUR_API_KEY"

@app.route('/chatbot', methods=['POST'])
def chatbot():
    user_message = request.get_json()['message']
    response = chatbot_response(user_message)
    return jsonify({'response': response})


def chatbot_response(user_message):
    response = openai.Completion.create(
        engine="text-davinci-002",
        prompt=user_message,
        max_tokens=1024,
        n = 1,
        temperature=0.5
    )
    return response['choices'][0]['text']

if __name__ == '__main__':
    app.run()

To integrate a chatbot with a frontend, use Flask to serve an HTML page with a form for user messages and the chatbot's answer. AJAX can submit the form to the /chatbot route, and JavaScript can show the chatbot's response.

I imported code snippets at the top of the file.

Let's add a frontend interface, I said.

CGPT:

<!DOCTYPE html>
<html>
<head>
    <title>AI Chatbot</title>
</head>
<body>
    <h1>AI Chatbot</h1>
    <form id="chatbot-form">
        <label for="message">Message:</label><br>
        <input type="text" id="message" name="message"><br>
        <input type="submit" value="Submit">
    </form> 
    <div id="chatbot-response"></div>

    <script src="https://ajax.googleapis.com/ajax/libs/jquery/3.5.1/jquery.min.js"></script>
    <script>
        $(document).ready(function() {
            $("#chatbot-form").submit(function(e) {
                e.preventDefault();
                var userMessage = $("#message").val();
                $.ajax({
                    type: "POST",
                    url: "/chatbot",
                    data: JSON.stringify({message: userMessage}),
                    contentType: "application/json; charset=utf-8",
                    dataType: "json",
                    success: function(response) {
                        $("#chatbot-response").text(response.response);
                    }
                });
            });
        });
    </script>
</body>
</html>

To serve this HTML page using Flask, build a new route that returns the page as a GET response.

So far, so good.

Looked quite basic so I got chatGPT to add some tailwind to the project.

Me: Tailwind the chatbot.html page, please. Give it a futuristic style with purple and neon

After a few more prompts, Talk GPT aligned the form to the center, changed some colors, and added padding.

CGPT:

<!DOCTYPE html>
<html>
<head>
    <title>AI Chatbot</title>
    <link href="https://unpkg.com/tailwindcss@^1.0/dist/tailwind.min.css" rel="stylesheet">
</head>
<body class="bg-black flex flex-col justify-center items-center">
    <h1 class="sm:text-center text-purple-500">AI Chatbot</h1>
    <form id="chatbot-form" class="border-purple-500 bg-purple-800 rounded">
        <label for="message">Message:</label><br>
        <input type="text" id="message" name="message" class="min-w-30 rounded"><br>
        <input type="submit" value="Submit" class="bg-purple-500 border-red-500 transform hover:scale-110 rounded">
    </form> 
    <div class="flex justify-center">
        <div id="chatbot-response" class="text-white rounded"></div>
    </div>

    <script src="https://ajax.googleapis.com/ajax/libs/jquery/3.5.1/jquery.min.js"></script>
    <script>
        var colors = ['red', 'orange', 'yellow', 'green', 'blue', 'indigo', 'violet'];
        var colorIndex = 0;
        
        $(document).ready(function() {
            setInterval(function() {
                $("#chatbot-form").css('border-color', colors[colorIndex]);
                colorIndex = (colorIndex + 1) % colors.length;
            }, 1000);

            $("#chatbot-form").submit(function(e) {
                e.preventDefault();
                var userMessage = $("#message").val();
                $.ajax({
                    type: "POST",
                    url: "/chatbot",
                    data: JSON.stringify({message: userMessage}),
                    contentType: "application/json; charset=utf-8",
                    dataType: "json",
                    success: function(response) {
                        $("#chatbot-response").text(response.response);
                    }
                });
            });
        });
    </script>
</body>
</html>

Improved:

A few more prompts like “Add more vertical and horizontal padding to the submit button and vertical margin, and vertically align this file's body.”

The result:

Is it effective? Now, I'll chat with ChatGPT's AI Chatbot. I intervened minimally throughout construction. Chat GPT created numerous files, connected and interacted with its own API, and presented the user request response on the front end by itself.

Me to AI Chatbot: Hey, can you give me 6 name suggestions for a black horse?

Me to AI Chatbot: Write a poem in the style of Jim Morrison. Make sure to mention cacti and black holes

ChatGPTs Chatbot:

In the desert night, I am confronted by cacti, 
Their arms reaching out, As if to grab me and take me away. 
The stars in the sky, Beckon me to come, 
To a world of black holes, Where I can be free. 
I am in a trance, My body and mind, 
In a state of limbo, As I wander the night. 
I hear a voice, Calling me to the unknown, 
I cannot resist, The lure of the black hole. 
The cacti watch, As I take my leave, 
To a place of mystery, Where I can find peace.

Of course, the next question I gave it was to build a chatbot!

Me: Build a python and flask AI chatbot that responds to user messages on the frontend.

ChatbotGPTs:

import os from flask 
import Flask, request, jsonify 
from chatterbot 
import ChatBot 
from chatterbot.trainers 
import ListTrainer 

# Create a new chatbot 
bot = ChatBot( 
  "My Bot", 
  storage_adapter="chatterbot.storage.SQLStorageAdapter", 
  logic_adapters=[ 
    "chatterbot.logic.BestMatch", 
    { "import_path": "chatterbot.logic.BestMatch", 
      "statement_comparison_function": "chatterbot.comparisons.levenshtein_distance", 
       "response_selection_method": "chatterbot.response_selection.get_first_response" } 
    ], 
    database_uri="sqlite:///database.sqlite3" ) 

# Train the chatbot with a few sample conversations 
conversation = [ "Hello", "Hi there!", "How are you doing?", "I'm doing great.", "That is good to hear", "Thank you.", "You're welcome." ] 
trainer = ListTrainer(bot) trainer.train(conversation) 

# Create a Flask app 
app = Flask(__name__) 

# Define a route for the default URL 
@app.route("/") def index(): return "<h1>Chatbot</h1>" 

# Define a route for the /get_response URL 
@app.route("/get_response", methods=["POST"]) 

def get_response(): 
# Get the user's message 
user_message = request.form["user_message"] 
# Get the bot's response 
bot_response = bot.get_response(user_message) 
# Return the bot's response 
return str(bot_response) 
# Run the Flask 
app if __name__ == "__main__": app.run()

No matter how many times I tried, the second generation always used chatterbot instead of the ChatGPT API. Even when I told it to use the ChatGPT API, it didn't.

ChatGTP's ability to reproduce or construct other machine learning algorithms is interesting and possibly terrifying. Nothing prevents ChatGPT from replicating itself ad infinitum throughout the Internet other than a lack of desire. This may be the first time a machine repeats itself, so I've preserved the project as a reference. Adding a requirements.txt file and python env for easier deployment is the only change to the code.

I hope you enjoyed this.

This is arguably the best three-minute demonstration I've ever seen of anything. Derek Sivers turns a shaky video of a lone dancing guy at a music festival into a leadership lesson.

A leader must have the courage to stand alone and appear silly. But what he's doing is so straightforward that it's almost instructive. This is critical. You must be simple to follow!

Now comes the first follower, who plays an important role: he publicly demonstrates how to follow. The leader embraces him as an equal, so it's no longer about the leader — it's about them, plural. He's inviting his friends to join him. It takes courage to be the first follower! You stand out and dare to be mocked. Being a first follower is a style of leadership that is underappreciated. The first follower elevates a lone nut to the position of leader. If the first follower is the spark that starts the fire, the leader is the flint.

This link was sent to me by @ottmark, who noted its resemblance to Kurt Vonnegut's three categories of specialists required for revolution.

The rarest of these specialists, he claims, is an actual genius – a person capable generating seemingly wonderful ideas that are not widely known. "A genius working alone is generally dismissed as a crazy," he claims.

The second type of specialist is much easier to find: a highly intellectual person in good standing in his or her community who understands and admires the genius's new ideas and can attest that the genius is not insane. "A person like him working alone can only crave loudly for changes, but fail to say what their shapes should be," Slazinger argues.

Jeff Veen reduced the three personalities to "the inventor, the investor, and the evangelist" on Twitter.