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!

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

The comeback tour continues…

First, he founded a $47 billion co-working company (sorry, a “tech company”).

He established WeLive to disrupt apartment life.

Then he created WeGrow, a school that tossed aside the usual curriculum to feed children's souls and release their potential.

He raised the world’s consciousness.

Then he blew it all up (without raising the world’s consciousness). (He bought a wave pool.)

Adam Neumann's WeWork business burned investors' money. The founder sailed off with unimaginable riches, leaving long-time employees with worthless stocks and the company bleeding money. His track record, which includes a failing baby clothing company, should have stopped investors cold.

Once the dust settled, folks went on. We forgot about the Neumanns! We forgot about the private jets, company retreats, many houses, and WeWork's crippling. In that moment, the prodigal son of entrepreneurship returned, choosing the blockchain as his industry. His homecoming tour began with Flowcarbon, which sold Goddess Nature Tokens to lessen companies' carbon footprints.

Did it work?

Of course not.

Despite receiving $70 million from Andreessen Horowitz's a16z, the project has been halted just two months after its announcement.

This triumph should lower his grade.

Neumann seems to have moved on and has another revolutionary idea for the future of living. Flow (not Flowcarbon) aims to help people live in flow and will launch in 2023. It's the classic Neumann pitch: lofty goals, yogababble, and charisma to attract investors.

It's a winning formula for one investment fund. a16z has backed the project with its largest single check, $350 million. It has a splash page and 3,000 rental units, but is valued at over $1 billion. The blog post praised Neumann for reimagining the office and leading a paradigm-shifting global company.

Flow's mission is to solve the nation's housing crisis. How? Idk. It involves offering community-centric services in apartment properties to the same remote workforce he once wooed with free beer and a pingpong table. Revolutionary! It seems the goal is to apply WeWork's goals of transforming physical spaces and building community to apartments to solve many of today's housing problems.

The elevator pitch probably sounded great.

At least a16z knows it's a near-impossible task, calling it a seismic shift. Marc Andreessen opposes affordable housing in his wealthy Silicon Valley town. As details of the project emerge, more investors will likely throw ethics and morals out the window to go with the flow, throwing money at a man known for burning through it while building toxic companies, hoping he can bank another fantasy valuation before it all crashes.

Insanity is repeating the same action and expecting a different result. Everyone on the Neumann hype train needs to sober up.

Like WeWork, this venture Won’tWork.

Like before, it'll cause a shitstorm.

New social media producers' biggest error

The Treadmill of Social Media Content

New creators focus on the wrong platforms.

They post to Instagram, Twitter, TikTok, etc.

They create daily material, but it's never enough for social media algorithms.

Creators recognize they're on a content creation treadmill.

They have to keep publishing content daily just to stay on the algorithm’s good side and avoid losing the audience they’ve built on the platform.

This is exhausting and unsustainable, causing creator burnout.

They focus on short-lived platforms, which is an issue.

Comparing low- and high-return social media platforms

Social media networks are great for reaching new audiences.

Their algorithm is meant to viralize material.

Social media can use you for their aims if you're not careful.

To master social media, focus on the right platforms.

To do this, we must differentiate low-ROI and high-ROI platforms:

Low ROI platforms are ones where content has a short lifespan. High ROI platforms are ones where content has a longer lifespan.

A tweet may be shown for 12 days. If you write an article or blog post, it could get visitors for 23 years.

ROI is drastically different.

New creators have limited time and high learning curves.

Nothing is possible.

First create content for high-return platforms.

ROI for social media platforms

Here are high-return platforms:

1. Your Blog - A single blog article can rank and attract a ton of targeted traffic for a very long time thanks to the power of SEO.

2. YouTube - YouTube has a reputation for showing search results or sidebar recommendations for videos uploaded 23 years ago. A superb video you make may receive views for a number of years.

3. Medium - A platform dedicated to excellent writing is called Medium. When you write an article about a subject that never goes out of style, you're building a digital asset that can drive visitors indefinitely.

These high ROI platforms let you generate content once and get visitors for years.

This contrasts with low ROI platforms:

1. Twitter

2. Instagram

3. TikTok

4. LinkedIn

5. Facebook

The posts you publish on these networks have a 23-day lifetime. Instagram Reels and TikToks are exceptions since viral content can last months.

If you want to make content creation sustainable and enjoyable, you must focus the majority of your efforts on creating high ROI content first. You can then use the magic of repurposing content to publish content to the lower ROI platforms to increase your reach and exposure.

How To Use Your Content Again

So, you’ve decided to focus on the high ROI platforms.

Great!

You've published an article or a YouTube video.

You worked hard on it.

Now you have fresh stuff.

What now?

If you are not repurposing each piece of content for multiple platforms, you are throwing away your time and efforts.

You've created fantastic material, so why not distribute it across platforms?

Repurposing Content Step-by-Step

For me, it's writing a blog article, but you might start with a video or podcast.

The premise is the same regardless of the medium.

Start by creating content for a high ROI platform (YouTube, Blog Post, Medium). Then, repurpose, edit, and repost it to the lower ROI platforms.

Here's how to repurpose pillar material for other platforms:

1. Post the article on your blog.

2. Put your piece on Medium (use the canonical link to point to your blog as the source for SEO)

3. Create a video and upload it to YouTube using the talking points from the article.

4. Rewrite the piece a little, then post it to LinkedIn.

5. Change the article's format to a Thread and share it on Twitter.

6. Find a few quick quotes throughout the article, then use them in tweets or Instagram quote posts.

7. Create a carousel for Instagram and LinkedIn using screenshots from the Twitter Thread.

8. Go through your film and select a few valuable 30-second segments. Share them on LinkedIn, Facebook, Twitter, TikTok, YouTube Shorts, and Instagram Reels.

9. Your video's audio can be taken out and uploaded as a podcast episode.

If you (or your team) achieve all this, you'll have 20-30 pieces of social media content.

If you're just starting, I wouldn't advocate doing all of this at once.

Instead, focus on a few platforms with this method.

You can outsource this as your company expands. (If you'd want to learn more about content repurposing, contact me.)

You may focus on relevant work while someone else grows your social media on autopilot.

You develop high-ROI pillar content, and it's automatically chopped up and posted on social media.

This lets you use social media algorithms without getting sucked in.

Thanks for reading!

Unleash the power of the Option key ⌥

#1 Open a link in the Private tab first.

Previously, if I needed to open a Safari link in a private window, I would:

• copied the URL with the right click command,

• choose File > New Private Window to open a private window, and

• clicked return after pasting the URL.

I've found a more straightforward way.

Right-clicking a link shows this, right?

Hold option (⌥) for:

Click Open Link in New Private Window while holding.

Finished!

#2. Instead of searching for specific characters, try this

You may use unicode for business or school. Most people Google them when they need them.

That is lengthy!

You can type some special characters just by pressing ⌥ and a key.

For instance

• ⌥+2 -> ™ (Trademark)
• ⌥+0 -> ° (Degree)
• ⌥+G -> © (Copyright)
• ⌥+= -> ≠ (Not equal to)
• ⌥+< -> ≤ (Less than or equal to)
• ⌥+> -> ≥ (Greater then or equal to)
• ⌥+/ -> ÷ (Different symbol for division)

#3 Activate Do Not Disturb silently.

Do Not Disturb when sharing my screen is awkward for me (because people may think Im trying to hide some secret notifications).

Here's another method.

Hold ⌥ and click on Time (at the extreme right on the menu-bar).

Now, DND is activated (secretly!). To turn it off, do it again.

Note: This works only for DND focus.

#4. Resize a window starting from its center

Although this is rarely useful, it is still a hidden trick.

When you resize a window, the opposite edge or corner is used as the pivot, right?

However, if you want to resize it with its center as the pivot, hold while doing so.

#5. Yes, Cut-Paste is available on Macs as well (though it is slightly different).

I call it copy-move rather than cut-paste. This is how it works.

Carry it out.

Choose a file (by clicking on it), then copy it (⌘+C).

Go to a new location on your Mac. Do you use ⌘+V to paste it? However, to move it, press ⌘+⌥+V.

This removes the file from its original location and copies it here. And it works exactly like cut-and-paste on Windows.

#6. Instantly expand all folders

Set your Mac's folders to List view.

Assume you have one folder with multiple subfolders, each of which contains multiple files. And you wanted to look at every single file that was over there.

How would you do?

You're used to clicking the ⌄ glyph near the folder and each subfolder to expand them all, right? Instead, hold down ⌥ while clicking ⌄ on the parent folder.

This is what happens next.

Everything expands.

View/Copy a file's path as an added bonus

If you want to see the path of a file in Finder, select it and hold ⌥, and you'll see it at the bottom for a moment.

To copy its path, right-click on the folder and hold down ⌥ to see this

Click on Copy <"folder name"> as Pathname to do it.

#7 "Save As"

I was irritated by the lack of "Save As" in Pages when I first got a Mac (after 15 years of being a Windows guy).

It was necessary for me to save the file as a new file, in a different location, with a different name, or both.

Unfortunately, I couldn't do it on a Mac.

However, I recently discovered that it appears when you hold ⌥ when in the File menu.

Yay!

Quick, easy and tasty (and dollops of parenting around food).

My wife and mom are both great mothers. They're super-efficient planners. They soak and ferment food. My 104-year-old grandfather loved fermented foods.

When I'm hungry and need something fast, I waffle to the pantry. Like most people, I like to improvise. I wish I knew these 11 hacks sooner.

1. The world's best pasta sauce only has 3 ingredients.

You watch recipe videos with prepped ingredients. In reality, prepping and washing take time. The food's taste isn't guaranteed. The raw truth at a sublime level is not talked about often.

Sometimes a radical recipe comes along that's so easy and tasty, you're dumbfounded. The Classic Italian Cook Book has a pasta recipe.

One 28-ounce can of whole, peeled tomatoes, one medium peeled onion, and 5 tablespoons of butter. And salt to taste.

Combine everything in a single pot and simmer for 45 minutes, uncovered. Stir occasionally. Toss the onion halves after 45 minutes and pour the sauce over pasta. Finish!

This simple recipe fights our deepest fears.

Salt to taste! Customized to perfection, no frills.

2. Reheating rice with ice. Magical.

Most of the world eats rice. I was raised in south India. My grandfather farmed rice in the Cauvery river delta.

The problem with rice With growing kids, you can't cook just enough. Leftovers are a norm. Microwaves help most people. Ice cubes are the frosting.

Before reheating rice in the microwave, add an ice cube. The ice will steam the rice, making it fluffy and delicious again.

3. Pineapple leaf 

if it comes off easy, it is ripe enough to cut. No rethinking.

My daughter loves pineapples like her dad. One daddy task is cutting them. Sharing immediate results is therapeutic.

Timing the cut has been the most annoying part over the years. The pineapple leaf tip reveals the fruitiness inside. Always loved it.

4. Magic knife words (rolling and curling)

Cutting hand: Roll the blade's back, not its tip, to cut.

Other hand: If you can’t see your finger tips, you can’t cut them. So curl your fingers.

I dislike that schools don't teach financial literacy or cutting skills.

My wife and I used scissors differently for 25 years. We both used the thumb. My index finger, her middle. We googled the difference when I noticed it and laughed. She's right.

This video teaches knifing skills:

5. Best advice about heat

If it's done in the pan, it's overdone on the plate.

This simple advice stands out when we worry about ingredients and proportions.

6. The truth about pasta water

Pasta water should be sea-salty.

Properly seasoning food separates good from great. Salt depends is a good line.

Want delicious pasta? Well, then kind of a lot, to be perfectly honest.

7. Clean as you go

Clean blender as you go by blending water and dish soap.

I find clean as you go easier than clean afterwords. This easy tip is gold.

8. Clean as you go (bis)

Microwave a bowl of water, vinegar, and a toothpick for 5 minutes.

2 cups water, 2 tablespoons vinegar, and a toothpick to prevent overflow.

5-minute microwave. Let the steam work for another 2 minutes. Sponge-off dirt and food. Simple.

9 and 10. Tools,tools, tools

Immersion blender and pressure cooker save time and money.

Narrative: I experienced fatherly pride. My middle-schooler loves science. We discussed boiling. I spoke. Water doesn't need 100°C to boil. She looked confused. 100 degrees assume something. The world around the water is a normal room. Changing water pressure affects its boiling point. This saves energy. Pressure cooker magic.

I captivated her. She's into science and sustainable living.

Whistling is a subliminal form of self-expression when done right. Pressure cookers remind me of simple pleasures.

Your handiness depends on your home tools. Immersion blenders are great for pre- and post-cooking. It eliminates chopping and washing. Second to the dishwasher, in my opinion.

11. One pepper is plenty

A story I share with my daughters.

Once, everyone thought about spice (not spicy). More valuable than silk. One of the three mighty oceans was named after a source country. Columbus sailed the wrong way and found America. The explorer called the natives after reaching his spice destination.

It was pre-internet days. His Google wasn't working.

My younger daughter listens in awe. Strong roots. Image cast. She can contextualize one of the ocean names.

I struggle with spices in daily life. Combinations are mind-boggling. I have more spices than Columbus. Flavor explosion has repercussions. You must closely follow the recipe without guarantees. Best aha. Double down on one spice and move on. If you like it, it's great.

I naturally gravitate towards cumin soups, fennel dishes, mint rice, oregano pasta, basil thai curry and cardamom pudding.

Variety enhances life. Each of my dishes is unique.

To each their own comfort food and nostalgic memories.

Happy living!