Hi, my name is Kathryn and I procrastinate.

Hopefully, right now, you’re thinking, No way. You deliver the O’Daily to my inbox every week on time.

But you also might be thinking, This does seem thrown together so that checks out. 😂😳

I used to hate my procrastination. I would be insanely jealous of my college friends who would be done with papers on TUESDAY for a Friday deadline. 🤯🤯🤯

I would sit down at my laptop on Tuesday night, committed to getting it done.

Four hours of Facebook later (it was still cool, okay?), I would head to bed with barely an outline.

Then I read this amazing essay by John Perry on “Structured Procrastination” that changed everything.

tl;dr — expect your procrastination. use it to your advantage.

How Structured Procrastination Works

1. Make a list of tasks in priority order
2. Do everything else on the list to avoid #1
3. Behold your amazing productivity and empty to-do list (except for 1 item)!

But…you didn’t get #1 done?!?

No problem.

1. Find an item that’s MORE important than #1
2. Tackle item-formerly-known-as-#1 to avoid doing new item #1
3. Congratulations! Your procrastination is helping you get shit done!

3 Ways To Activate “Structured Procrastination”

1. Create deadlines.

Schedule a meeting, tell someone you will have it by a certain date, hire a coach, make an accountability pod, sign up for a pitch competition, whatever will feel “real” and create pressure on your to-do list.

2. Leverage your “Tendency.”

I am an Upholder/Obliger. So I *KNOW* that I keep my commitments to others. When something is important, I promise someone I will do it.

3. Use calendar blocks (to know you’re behind).

I use calendar blocks to help me visualize the actual time I have to complete a task or project. A Thursday deadline becomes urgent on Monday when I clearly see I’m booked with meetings on Tuesday and Wednesday.

Procrastination and Long-Term Goals

You might be asking, but Kathryn, how could you train for Ironmans as a procrastinator???

Or maybe you’re thinking, how the hell can I build a big ass company — a 10 year endeavor — when I procrastinate??

Here’s what’s worked for me — set up systems that make it easy to do the right thing.

I didn’t think of Ironman training as “I’m going to do this really hard thing today and then repeat it every day until forever.”

I met my friends for a bike ride. I went to Masters Swim practice. I did what my coach wrote in the training plan.

A lot of it was “show up” and then let habit (and peer pressure!) carry you.

Same can be true for startups and company-building.

Here are common accountability mechanisms:

• customer meetings/deliverables
• investor updates
• board meetings
• quarterly (monthly, weekly, daily) sales targets
• weekly team meetings
• daily standups
• product roadmaps/releases
• internal meetings about high priority projects

Some of these naturally occur, some will be cultivated as you grow, and some you may want to add intentionally today!

Trust Your Procrastination

I’m such a sophisticated procrastinator that I keep a 3 item to-do list.

Let me explain.

I never put “clean the car” on my to-do list.

I know myself well enough to trust that I will suddenly, urgently need to vacuum the car 15 minutes before we leave for a road trip.

Don’t force that gnarly chore on a laid back family weekend.

Same with wiping down ceiling fans, cleaning out photos, updating old blog posts, and whatever other crappy task I *should* do but just can’t make myself at the moment.

Enjoy the Guilt

All the anti-procrastinators right now:

But Kathryn — it feels so good to get your stuff done instead of having it hang over you!

Allow me to offer a different perspective.

I like the guilt.

When you read a blog when you *should* be replying to emails, it’s so much more indulgent and enjoyable!  

I’m going to treat myself. I stole this time! How luxurious to read the O’Daily.

If I’m already at Inbox Zero, I tend to meander aimlessly around Slack or LinkedIn. No productive learning or stolen moments of fun.

LAME.

It reminds me of the meeting cancelation paradox:

• Have 30 minutes open on your calendar? → That’s nice.
• Someone cancels a 30 minute meeting? → OMG WHAT WILL I DO WITH ALL THIS EXTRA TIME??

Instead of guilt, embrace the joy of procrastinating!

Repeat after me:

”I work well to deadline.”
”I know I’ll get it done when it matters.”
”I love using my procrastination to be productive and have fun.”
”I don’t beat myself up for procrastinating, I revel in it!”

Procrastination: Another Way to Say No

I spend a lot of time (practicing how to get better at) saying no:

• why to say no
• 7 ways to say no
• 4 more ways to say no
• how to say no to your boss
• how to have fewer meetings
• how to prioritize (aka figure out when to say no)

Procrastination is a secret, subconscious way to say no.

You say no when you have to. Because you ran out of time to do only the most important things!

It’s also a great way to say no to perfectionism and yes to shipping!

You may want 20 hours to perfect your slide deck but if you only have 2 hours, you figure out a way.

It’s not perfect but it’s live in the world which is 100x more important than perfect, especially at startups!

My 3 Steps To Blog Every Week

So how the heck to I get my blog out every week?

STEP 1: I tell my wonderful readers that I will email them on Tues. They are counting on me!!! (My Obliger tendency believes this. Reality is irrelevant. 😂)

STEP 2:  I schedule a calendar block and stick to it — no meeting creep!

STEP 3: **where the magic happens** I include time in my calendar block for Inbox Zero and other random productive tasks to make the most of my structured procrastination!

What tips or strategies do you use to avoid or leverage your procrastination??

‍

Are your customers mad at you?

Congratulations!!!!!!

You have built something that:

• people want
• is relevant to their daily life
• costs money
• can’t be easily replaced

It’s the first step to product market fit!

Beware of “Quiet Quitting”

“Quiet quitting” is the most dangerous activity possible to a company.

I’m not talking about employees (though that’s not good either).

I’m talking about customers who leave without telling you.

Customers “quiet quitting” means:

• They don’t care enough to be mad.
• They’re not financially invested enough to try to “get their money’s worth.”
• They don’t have enough loyalty to you or your brand to give feedback.

Why would this happen?

• Maybe it’s not a mission-critical service you provide.
• Maybe there’s a cheaper, better option that’s easy to switch to.
• Maybe they don’t have enough skin in the game (aka you’re significantly under charging or — GASP—giving away your product for free. 😲)

Stress, Celebrate, Resolve

When you have your first upset customer, follow these 3 steps:

1. Totally stress out. It’s a normal, visceral reaction. If you care, you will immediately have some level of “OMG” panic even if it’s a split second.

2. Remind yourself it’s a good thing. Then you’ll think about this post and realize it’s a CELEBRATORY EVENT!

Someone really cares about this product and the problem we’re trying to solve!

3. Respond to the customer ASAP. You may or may not be able to fix it but a quick response and willingness to listen will make a huge impact.

Training Resource

For a quick overview of what to do when customers are upset, here’s a Customer Service 101 Training Deck (customizable to your company) from our Customer Success Starter Pack.

A Future Champion

Your upset customer, assuming they’re a reasonable human with a valid complaint, is a terrific prospect for a future advocate and source of referrals!

How To Make A Customer Love You:

1. Respond quickly.
2. Listen deeply.
3. Give updates about your plan of action.
4. Solve the issue or incorporate the feedback.
5. Make an advocate for life!

You’d be surprised how rarely companies follow those simple steps and what an impact it can have on customer loyalty.

So when you have your first angry customer, not only is a moment of celebration, it’s also a great time to practice your turn-them-into-a-future-champion workflow!

What have you learned from angry customers? Did you have any counter-intuitive signs of success or progress?

‍

Last week, I got to dive deep on a favorite topic at Women + Tech in the Atlanta Tech Village —> building BIG companies!

We talked about:

• What “big” means
• Why it matters
• How you actually do it
• And —**BONUS** — the 2 secrets that make all the difference

Here’s the FULL SLIDE DECK with a bulleted summary below.

The only thing missing are my awesome jokes (LOLZ) and the great audience questions.

You have to be in-person for those! 😂

GO BIG: The What, Why, and How of Building a Billion Dollar Business

The Ah-Ha → Think Bigger!

• Where are all the women (in VC and large startups)??
• Many social, external things holding women back
• Within our control? More women thinking big!
• Look in the mirror → I need to think bigger too.
• BHAG set: 10 female-founded unicorns in the Southeast in the next 10 years

The What → Unicorns

• $1B valuation
• $100M ARR
• ~10 years to build
• 500-1000 employees
• 10% employee option pool
• 10% - 75% owned by the founder (depending on funding rounds)

The Why → Huge Impact

• $100M to employees
• $100M - $750M to you (founder)
• Help thousands/millions of customers
• Make the world better
• Be an example, open doors for others
• Generational wealth, philanthropy, investor

The SECRET → Bigger Is Not Harder

• It’s hard to build a small company too. (Ask any entrepreneur!)
• Building a big company is not 10-1000x harder.
• But the impact is 10-1000x bigger.

P.S. Women do tons of hard stuff all the time!

The HOW → Big Market, Start Small

1. Pick a BIG market

• Small but growing. Think billions + trillions!
• Software has great margins + scale.
• Competition is good.
• Small slice of a big pie.
• Be in the path to revenue.

BIG Market Examples: aging in place (and more here), robotics, creator economy, healthy fast food, carbon tracking

2. Start SMALL

• Read “The Mom Test” by Rob Fitzgerald
• DO NOT build tech to start!!!!!!
• Follow the money.
• Look for authentic demand.

3. Start a Tech Company…Without Tech

• Social post (Greenzie)
• Waitlist sign up (Atlanta Ventures Studio)
• Community of target users (Salesloft)
• Manually solve it (Carpool Logistics, AdPipe)
• Consulting (Unboxt, Zinnia)
• Customers pay upfront

Spoiler Alert: You can learn tech or find a co-founder! Many tech founders and CEOs are not engineers.

THE HOW → 10 Tips To Raise Money

1. WATCH: The real reason female entrepreneurs get less funding (Dana Kanze)
2. Talk about The Money
3. Show **real** customer traction (not pipeline or hypotheticals)
4. Know your metrics & industry metrics
5. Go to Pitch Practice → pitchpractice.co
6. Prep for Q&A
7. Pitch your worst first
8. Lines not dots
9. Who has $$ that cares about this problem?
10. HAVE YOUR CUSTOMERS PAY YOU!!!!!!!!!!!!!!!

THE HOW → Unicorn Founder Traits

• Learning - grow as your company grows
• Selling - sell to customers, investors, employees, future employees. You cannot outsource this! But you can learn it.
• Resilience - successful founders leave high paying jobs (and don’t go back 😜)
• Authenticity - do it in your own style, lean into your strengths
• BIG MARKETS! - great people who pick small ideas don’t build unicorns

THE (other) SECRET → Everyone Has Doubts

They seem wildly confident but even the most successful founders have doubts.

• “I got lucky.”
• “I don’t know what I’m doing.”
• “We’re making it up as we go.”
• “I hate public speaking.”

They do it anyway.

So can you!

What other advice do you have for building big???

If you attended, what was your favorite takeaway? Any that I didn’t mention in the recap?

‍

Looking to raise money?

First, talk about The Money. Alllllll the money to be made in your market.

This includes having a believable TAM/SAM/SOM analysis.

Then you wow with your amazing revenue dolla—WHAT? Not much revenue yet???

Never fear.

You can still project confidence and financial savvy to win investors over.

Showcase a precise and specific understanding of your business numbers to show investors that you can:

• Build a company with a sound business model
• Be responsible with cash
• Make data-driven decisions

It’s simple but it will set you apart!

Here are 4 strategies to showcase your business savvy regardless of your revenue!

1. Know Your Numbers

Maybe you don’t have much revenue. Every business, no matter how small or early, has tons of business data.

• How many deals and dollars are in your pipeline?
• How many cold calls are you making per day?
• The click thru rate on your most recent email?
• Exact monthly burn?
• How much you spent on <engineering, ads, events> last month?
• # of customers you’ve spoken to?

IMPORTANT NOTE — this doesn’t work if you’re wishy-washy.

Saying, “uh, about, 100 or so calls per day” does not have the same effect as, “I averaged 82 calls per day in May.”

Also, you can’t just have these numbers on a slide. You have to KNOW THESE NUMBERS in your heart and mind.

Add them in when answering a question or describing a revenue projection.  

It shows you understand that numbers, not just ideas or cool tech, drive a business.

2. Refer To Industry Data

Don’t have much of your own data? Wondering how to justify revenue projections or financial models?

POWER MOVE: Study publicly available financial data from companies like you.

Sources:

• S1s, 10-Ks, and other SEC filings (or recaps)
• Early pitch decks, presentations, podcasts from founders
• Industry benchmark reports (Bessemer has top notch info)
• Saastr and Lenny’s Newsletter have great case studies and insights

Then reference it frequently:

We assumed an x% conversion rate because that’s what LargeUnicorn saw in their first year.

OR

The average spend in this area from F500s is $1,512,000 per year, and that’s up from $1,279,000 in 2020.

OR

PublicCompany gets 42% of their customers from Instagram ads and another 17% from influencers so we’re planning to start with those two strategies.

3. Talk About Tests

Explain what tests you’ve run and the (numeric!) results.

Tests? What kind of tests?  

• 7 examples of low cost or free ways to test authentic demand
• 4 real life examples of testing product ideas without tech
• Anything where you set a hypothesis and analyze the outcome

Test results can be a helpful proxy for revenue or validate a strategy.

It gives investors confidence in your plan because it’s based on real world findings, not founder musings.

Make sure you talk about the specific numbers, dollars, conversion rates.

We did a waitlist sign up test. We spent $515 on ads, got 3,000 impressions, with 5% conversion rate. We called each person that signed up and connected with 17 of them. 9 of those committed to a paid beta test for $99/mo. So we spent $515 for $900 committed.

Don’t have amazing metrics like my made up test data? 😉 Even something like this can be great:

We’ve had 95 conversations with VPs of Engineering at mid-size tech companies. Of those, 37 agreed to a follow up meeting. In those follow ups, 9 said they would have budget to solve this problem.

4. Explain Your Assumptions

This is where you combine #1-3 to show that you’re thinking deeply and (somewhat) realistically about the future of your business.

Similar to our TAM/SAM/SOM tip of “Show Your Work”, use your data, industry data, and test data to explain why you think you can do $1M in revenue by year 2 or why you can get your profit margin to 40% when you’re selling 10,000 units.

Based on our test campaign with a 10% response rate & 5 demos scheduled, competitors charging $1000/mo, and the growth of this market by 200% last year, we think 10 new customers in our first quarter and 50 customers at $50,000 MRR by end of year with one sales hire is realistic.

It may sound obvious but you’d be surprised how many folks don’t know the details behind their financial projections or business model.

Do this from a position of strength by citing your supporting data and highlighting what’s fact vs. educated guess.

Explaining it with confidence while acknowledging hypotheses or unknowns can be a powerful way to build trust.

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Even when you don’t have much revenue, you can still impress investors and show you’re going to build a strong, financially-sound business.

Talk about numbers, drop juicy data points, and walk through your strategy and thought process with specific dollars, conversion rates, and metrics!  

What other strategies can early stage founders use to show off their business savvy??

‍

I meet thousands of entrepreneurs every year. Some I stay in touch with. Some I don’t.

What’s the difference between a one-time meeting and a long term relationship?

Here are 6 straight forward ways to build authentic relationships with an investor or other strategic partner for the long term.

1. Follow up.

Going to start with the basics. Send a follow up email.

A simple “thanks for the time” means that:

• we have an email thread for future correspondence
• I can search my email for your name and company details
• you’ve already stood out from 50% of folks

And you’ll REALLY nail it if you:

• Add one line of personalization — remembering a specific fact or tip
• Follow up with a link or article you mentioned
• Show that you’ve followed up on a suggestion or took notes
• Plant the seed for staying in touch

EXAMPLE:

It was great to connect today! I’ve already checked out the article you suggested and will see you at the next event at Atlanta Tech Village. Look forward to keeping you up to date with our progress. Do you mind if I add you to future company updates?  Hope you have a great trip with the family next weekend!

BOOM. 3 minute investment for a potential long term relationship.

2. Add them to a regular update email.

I love an email update from a founder.

Send it (bcc) to everyone you want to stay in touch with.

Like a newsletter only way simpler. Bullets are great. No need to mess with graphics or fancy headers.

Remember to include:

• What We Do Again: one sentence blurb. Early stage companies have frequent name changes and product pivots so help an investor out!
• Asks: intros, open roles, or other help you need. Great way to test potential investors or advisors to see who is actually helpful.
• Thank You’s: specific shout outs. Everyone loves to be recognized, even (especially?) jaded investors 😉 Often times, it will make people work even harder for you!
• Progress: Brag on yourself. Show graphs of growth. Share learnings. Don’t be modest - tell the best stuff! Quotes from customers are a great validation and storytelling strategy.

Paperstreet and Cabal are two tools I see that make an update easy.

Also — don’t worry too much about a regular cadence. Send an update when you can, when you have something to share or ask for. Everyone is too busy to keep track of when you sent the last one!

There are companies that I’ve met once but I’m on their update and feel like I know them. I’ve gotten a regular email from their founder and tracked their progress over months and years.

It’s like a blog, hitting your inbox every week. 😉

3. Ask for advice.

It may sound counter-intuitive but it’s better to ask for advice than act like you know it all.

People build more rapport and trust with people they help vs. people who have helped them.

Asking for advice shows:

• You want to learn and grow
• You’re smart enough to ask good questions
• The investor can be helpful to you (investors like to add value)

BUT — it’s important to ask for advice in the right way!

Best way to ask for advice:

• Do some preliminary research.
• Show that you at least know someone’s professional background or have looked up an article or two on the topic you’re asking about.
• Be specific with your ask.
• YES: “I’d like to pick your brain about scaling customer success.”
• PLEASE NO: “I’d like to pick your brain. Can I have an hour of your time to think aloud and muddle through my questions?”
• If you can share relevant info or questions ahead of time, even better!

A pretty common superpower of successful founders (in addition to testing hypotheses) is to be great at specific requests for advice or help.

Start practicing this skill now!

4. Go to events they regularly attend. Say hi.

I notice and appreciate the folks who show up every time. I learn their names. I see them and wave. They stay top of mind.

Never underestimate the power of simply SHOWING UP regularly.

Once you see someone a few times, it’s easier to strike up a conversation. You feel as if you know them. You have more to talk about.

It’s the human version of the Marketing Rule of 7.

Also, anyone who hosts events regularly genuinely appreciates consistent attendees.

Here’s the key → make sure you say hi!

• Catch their eye and wave.
• Send them a chat via Zoom.
• Send a quick follow up email.
• Don’t force a conversation if they are tied up but make sure they see you!

If you go to an event but no one knows you’re there, did it even count??? (Nope.)

Where will a VC be?

• Wherever their marketing person tells them to. 😂😂😂 But, seriously, a firm-sponsored event is a great place to start.
• Check their LinkedIn or Twitter to see if they’ve promoted or mentioned any upcoming events.
• Feel free to ask them. It’s a great touch point and easy for everyone to coordinate.

Fun story:

I knew a great sales rep who used a variation of this tactic to build relationships with C-level folks.

Her approach:

1. Send an email saying congrats on a recent award or event
2. Write a hand written note
3. Connect via LinkedIn
4. Introduce herself at an event

By then, they’d recognize her name and feel like they must have met her somewhere before!

5. Share content or events.

Now that I’m an experienced, world-renown blogger (LOLZ), I really understand this.

Everyone appreciates a shout out, a share, or a kind comment!

Do it on the socials or send them a direct note.

It’s also a great way to meet someone. They’ll recognize your name even if you haven’t met in person.

Even well-known folks, who have an empire of content or success, notice who regularly comments or amplifies their message.

6. Be genuine.

Never underestimate the power of authenticity and being nice!  It’s my favorite not-networking strategy.

Don’t try to be a certain type of founder or copy someone else.  What works for them will be weird for you.

Even the most spreadsheet-focused investor appreciates a human connection and can spot a jerk, schmuck, or forcing it.

Are you a great storyteller? Do that. More of a listener than a talker? Fantastic.

There’s no “right” way to network. Be the best version of yourself and do what makes you shine.

CAVEAT: Everyone has imposter syndrome so just ignore that and lead with confidence. 😁💪

Founders — what other strategies have helped you build relationships with investors?

Investors — what strategies work best to build a relationship with you?

‍

Do I know about podcasts?

Absolutely not!

That’s why Adam Walker, a great entrepreneur, podcaster, thinker, and writer, is joining us today as a guest blogger!

Adam and I have been trading productivity tips, book recs, and startup advice for years. I hope you love his energy, humor, and clarity of thought as much as I do.

You can subscribe to his fantastic Substack here and check out his podcasts, Tech Talk Y’all and Real Pink.

And, of course, check out the O’Daily guest post on Adam’s Substack! 😉

Podcasting Made Easy: Your Simple How-To Guide

By Adam Walker

Why Should I Start A Podcast?

Starting a podcast is easier than you think and could be more valuable. But before I tell you how to start a podcast, let's discuss why.

Here are 3 quick reasons you might consider becoming a podcaster:

1. Sales and Networking

People hate cold calls (and cold emails), but most people love to get interviewed and share their knowledge. If you need to meet high-level people to get ahead, a podcast will get you those meetings.

2. Thought Leadership

You are an expert and want to share your knowledge, positioning yourself as a thought leader in your space.

3. Create Marketing Content

This is the most underrated use of a podcast. A good podcast will produce a lot of original and interesting material, so why not take that material and create more marketing assets from it? One podcast episode can become up to 15 pieces of marketing content, like videos for YouTube, TikTok, and Instagram. Graphics for Facebook and LinkedIn. Or blog posts and transcripts for SEO on your website.

How do you start a podcast?

Ok, now let's talk about how to get started. Below is your quick start guide.

1. Decide what kind of podcast you are creating.

What is the topic? Who is the audience? Will you interview people or not?

2. Determine your goals.

Will you use your podcast to book meetings with the right people? Do you want to create all of your social media assets from your podcast? Do you want to build an audience? Ensure your goals are clear from the start so you can craft your podcast towards them.

3. Start recording.

I'll be honest; this is one of the hardest parts. You always feel like you need more time to record, but you have to make yourself start. Record an episode or two just to see how it goes. And give yourself permission to scrap through the first few episodes if needed.

4. Edit.

I'll talk more about tools in a minute, but for now, know that editing a podcast is doable, and there are many tutorials on YouTube to help.

5. Publish and get feedback.

Even when the episode doesn't feel ready, you must publish it and get feedback. It's the only way to start and grow a podcast.

What do I need to start a podcast?

To start a podcast, you need less than you think. Below is a quick list of the basics to get you started.

1. Guest Management Tools

If you will have a podcast with guests on it, the most important tool you need to make your life easier is Calendly. Calendly will let guests book their own recording time and send them emails with details about the recording.

2. Recording Software

You probably already have the recording software you need. If you are recording a solo show, you can use Garage Band, Quicktime, or any local program to capture audio.

If you are recording an interview show, Zoom works great, or if you want an upgrade, you can check out Riverside.fm.

3. Recording Gear

You don't need to spend a lot here; just get started. I recommend starting with a good webcam (Anker PowerConf C302) and microphone (Samsung Q2U).

You can go up from there, but this will give you a solid starting point to create a great show.

4. Editing Tools

Audacity is a free tool you can use to edit audio. My first podcast (Tech Talk Y'all) was edited on Audacity for years, and it was great. But if you want an upgrade that isn't too expensive, I strongly recommend using Reaper. Reaper can edit audio and video, and there are a lot of YouTube tutorials available to teach you how to use it.

5. Publishing

Publishing a podcast is free with Spotify for Podcasters (formerly Anchor.fm). Through Spotify for Podcasters, you will be about to publish your show on Spotify, Apple Podcasts, Google Podcasts, and many other platforms.

Ready, Set, PODCAST!

Podcasts are popular for a reason. They communicate information quickly, are entertaining, and can act as the centerpiece for all your marketing content. There has never been a better time to start one, so if you are interested, give it a shot.

And, if after reading this article you still aren’t sure where to start, you can read a more in-depth post from me on this subject here. Or, schedule a time to have a podcasting chat with me here.

Subscribe to Adam's Substack

As a reminder, this post was written by O’Daily friend, Adam Walker. To read more of Adam’s work, be sure to subscribe to his Substack here, or visit his personal website here.

Thanks, Adam, for the amazing podcast overview and how-to guide!

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Other podcast advice to share?? If you’ve started a podcast, how did it go?

Did you like the guest post format? Who should we invite next?

‍

We recently talked about the absolute best way to pitch investors and how to dominate your market analysis during a pitch.

This was for venture investors (aka “VCs”).

Are you talking to strategic investors?

Take that previous advice and THROW IT AWAY.

I got first-hand, real world tips from a company that recently raised from strategic investors (or “Strategics” as we say in the biz).

• What did they learn?
• What was different between VC + “Strategics”?
• What advice would they give?

Here is everything you wanted to know —and more — about the strategic investment process, directly from founders who successfully raised money.

What is a Strategic Investor?

Here’s a helpful fancy-pants overview.

The gist:

• Usually a large company with a “venture” or “innovation” department
• Natural alignment — usually have the same customer or industry
• Potential acquirer down the road
• They put in investment money but don’t care much about controls or valuation

What’s in it for them?

• They keep tabs on new innovation
• Cross-sell or integration opportunities
• Try before they buy
  

How is the pitch deck different for Strategic Investors?

(1) Less focus on the overall market size. 

• TAM/SAM/SOM isn’t addressed (so disregard all this).
• The Strategic likely knows more about this than the company pitching them 😉

(2) More technical capabilities discussed.

• No basic tech intro.
• Expect a deep dive into expertise, operations, technology.

(3) More focus on alignment and strategic advantage.

• What our startup can do for you!
• Acceleration or expansion of internal projects is important to them.

(4) Customize each slide deck.

• Less information on Strategic’s competitors.
• Know their current priorities and initiatives.

What do Strategics care about?

(1) Their business.

Large companies will often invest, acquire, or partner to:

• Open new markets
• Increase speed to market
• Fill a strategic need internally they don’t have time or expertise to tackle

(2) Win-win outcomes.

• A collaborative relationship that leads to future growth for both partners.
• Less focus on monetary returns.

(3) Avoiding acquisition by a competitor.

• Even if it created a great financial return on their investment, they probably don’t want their largest competitor to scoop you up.
• Companies will invest (or even acquire) to prevent competition down the road.

(4) EBITDA.

• Some Strategics are very focused on when investment will produce EBITDA.
• Not used to a high growth (aka startup/VC) model where profitability is a tradeoff for gaining market share.
• Be ready to speak their language.

What is different about the investment process?

(1) Introduction and relationship building process takes longer with Strategics.

• Meet Strategics at a trade show, conference, or warm intro.
• Do not cold-call or send unrequested one-pager (which is typical and expected with VCs). 

(2) More investment in “Proof of Technology.”  

• Build (v1) technical integrations between startup and Strategic as part of the investment process.
• Startup may foot the bill and may not recover the expense.
• Worth it to do for Strategics but not VCs.

(3) More technical vetting.

• Calls with subject matter experts.
• Testing, validating, deep look under the hood.

(4) More in-person meetings. 

• Strategics visit startup.
• Startup visits Strategics. 
• Multiple trips.

Other key advice and learnings?

(1) The deal can die at any level.

• Strategic Investment team may only be 1-2 people. They are likely super excited to do a deal but investment is not a core business function of the larger organization.
• Process goes through many layers of internal approval (and external approval if the board is involved) → it can get vetoed at any level.
• It is not the same as a professional investment discussion. 
• Keep multiple irons in the fire and be prepared to win/sell at every meeting.

(2) General counsel can make investment documentation harder.

• Most VC deals use outside counsel.  
• Speed is the focus and terms are more standard with VCs.

(3) Things take longer than expected.

• Welcome to large corporates, folks.
• It’s true for investment process and internal adoption post-investment.

Exploring strategic investment?

Strategic investors can be incredible partners.

They have industry expertise, lots of customers, scalable systems and sales channels, and money to invest in new technologies.

They are a great option to consider when you’re fundraising.

Follow these tips to customize your approach and understand what matters most!

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Want more? How do you maximize your strategic relationship once you’ve partnered??

We’ll continue to add to this series with additional learnings from the front lines.

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Great pitches talk about The Money.

We shared two amazing examples last week.

These pitches both opened with a TAM/SAM/SOM analysis.

(What the heck is TAM/SAM/SOM? Read this, this, this.)

This market analysis an assessment of how big your business could be, usually shared during pitch.

In other words — how big is the pie? how big can your cherry-filled dollar-filled slice be???

There’s two kinds of market analyses:

1. Believable
2. Not believable

Guess which one is better?!?

(Did you say #1?🤞🤞🤞)

So why would someone end up with #2 and how can you improve to #1?

Here a 4 ways to crush your TAM/SAM/SOM — aka THE MONEY — analysis during a pitch!

1. Pick a credible TAM.

A common mistake is picking the wrong Total Addressable Market.

It’s a big TAM but not aligned or believable.

If you’re building a new Segway, it’s a (really, really big) stretch to say that you’ll capture 10% of the global automotive sales ($3.6T).

But how many people are riding bikes, taking public transportation, or live within 3 miles of their office? What if 10% of them switched to your hot new Segway?

Now, that feels reasonable. I’m starting to believe.

VCs like big markets. So definitely showcase the biggest market possible for the TAM — if — it makes sense.

If it’s too much of a stretch, the whole analysis loses credibility.

Show your vision, think big, and also make the logic rock-solid.

#PROTIP
Is your market small now but will grow significantly over the next 3-5 years? Explain why and how. VCs love expanding markets.

2. Do realistic math.

If we get just 10% of all F500 to pay us $10,000/mo, we’ll have $6,000,000 ARR in Year 1!

The math is correct. The assumptions are a stretch.

Yes, you believe in your product and some companies (including yours!) will grow insanely fast.

But you’ve got to factor in:

• People are slow to change.
• Big companies are harder to sell than you think.
• You haven’t stress-tested pricing.
• Product-market fit may need some iterations.

Investors appreciate unwavering confidence but it’s important to show you understand potential challenges and have (at least somewhat) realistic expectations.

#PROTIP
If you have early indicators that you can outpace typical startup results and growth rates, by all means, highlight these!

Comparing your metrics to the early metrics of big companies in a similar market (e.g. in year 2, Salesforce had x dollars of ARR, and we’re already at y) is a nice way to do this.  

3. Show your work.

Bringing it back to 4th Grade Math.

Walk through your thought process, assumptions, and data in each stage of TAM, SAM, SOM.

Founders often rush through this slide.

I’m not sure if it’s because it’s a “required” slide, they don’t want too many holes poked, or they assume investors already understand.

Here’s the thing.

If you’re building a B2B sales or marketing platform, I get it. 5 seconds and move on.

Anything else…spend at least a few moments walking through your thought process and data.

• Showcase your industry knowledge
• Give enough color commentary to make it feel “real.”
• Understand your audience and adjust detail and explanation accordingly.
  

You may have picked the right TAM (#1) and done realistic math (#2) but if you don’t walk us through the math, we won’t know how you got the market size answer!

#PROTIP
Valeria Brenner of Thryft Ship does an amazing job of this here. The detail shows that she deeply understands her customer, product, and market.

4. Evaluate your goals.

You pick the right TAM.
You do realistic math.
You show your work.

…and the market isn’t worth billions.

This is okay!

There’s many amazing businesses in the world of all sizes.

Most VCs look for companies that could do $100M ARR within 10 years and be valued at $1B or more. This requires a really big market in the billions and even trillions.

But some of the most successful entrepreneurs never go the VC route. They self-fund, lean into a niche, or build a cash-flowing business from day 1.

There’s many ways to succeed, change the world, love your life, and make lots of money!

So, have an honest conversation with yourself.

Do you want to build a really big company? Do you want to raise from venture capital?

YES?

• Rethink the opportunity and find a much bigger one!
• It may be a different market.
• It may be an expansion of your current idea.

Do you want to solve the current problem that you are wildly passionate about?

YES?

• Great! Stay the course but adjust the financing strategy.
• Raise from alternative capital sources, grants, crowdfunding, angel investors who care about this problem
• Or —crazy idea here — get customers to pay you! 😉
  

#PROTIP
VCs run their own (more conservative) analysis of TAM/SAM/SOM. Want to rigorously vet your idea ahead of time? Use this fantastic chart from A Smart Bear.

Market size is key to understanding how big a business can get.

Every investor is thinking about market size and doing their own analysis while you’re pitching.

Help them see what you see by walking through a well-researched, believable, rock-solid TAM/SAM/SOM analysis!

What tools or tips do you have for market sizing or TAM/SAM/SOM slides? How do you keep the market analysis clear yet concise in a pitch?

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What’s the #1 improvement founders can make to their pitch?

Talk MORE about money.

Talk about it early. Talk about it often.

This is especially true if you’re working in an industry or on a problem that most VCs don’t know or understand.

What do I mean?

A pitch equals 1000 O’Daily words.

Here are two amazing examples of pitches that #nailedit!

Big Money Pitch #1

Kara Smith Brown gives my favorite example.**

Here’s the pitch:

It’s a product used by half of the world’s population.
For 40 years of their life.
Every month.
7 days per month.
5-10 times per day.
No innovation in 50 years.

Every investor’s brain rn: HOW CAN I BE A PART OF THAT CASH COW????

What’s the product?

Tampons.

Dollar signs win over nervous laughter.

(Yes, women investors understand this problem but talking periods in a biz meeting is not the norm.)

Look at all the period products companies that have sprung up in the past 5 years. Someone figured out how to TALK ABOUT THE MONEY.

Kara experimentally pitched this to a group of men. All were leaning in and nodding after hearing the economics of the business.

Explain The Money to capture your audience.  

**NOTE: Kara doesn’t even own a period products company. She is the CEO of a supply chain lead gen firm. She is simply incredible at business and pitching.

Another great insight from Kara: talk more about revenue!!

Big Money Pitch #2

Valeria Brenner, CEO of Thryft Ship, gave the most amazing pitch last week at First Pitch Friday.

She opened by spending 2 minutes explaining the Instagram thrift market and how much money is being made every year in this space.

I don’t know much about Insta thrifting. As a Millennial geezer, I stick to Goodwill and ThredUp.

Without that opening TAM/SAM/SOM slide showing billions of dollars, I might have thought it was small potatoes and started brainstorming bigger markets for a talented entrepreneur like Valeria.

Hundreds of millions of dollars grabbed my attention.

She then flowed into more great data points:

• 6 figure revenue within a year
• bootstrapped
• while being a student

It was a fantastic pitch that led with The Money. It made all the difference!

How To Talk About “The Money”

“The Money” is:

• Market size
• Revenue
• Metrics
• How big this business can get, quantified in $$
• A hook to get investors engaged

“The Money” is not:

• How much you want to raise (mention at the end but not a focus)
• TAM/SAM/SOM with unreasonable assumptions
• Your budget
• A single slide (should be incorporated throughout)

Translate your company into the universal language of business → 💰DOLLARS💰

Grab the attention of an investor by showcasing how big the opportunity is early and often!

Want more tips on pitching, fundraising, and what investors care about?

Coming soon:

• Dos and Don’ts of TAM/SAM/SOM slides
• How to talk about The Money when you’re pre-revenue
• What to know about the hearts & souls of investors (yes, we do have them 😉)
• 2 foolproof ways to “wow” in an investor meeting

…and more!

What’s been most effective when you’re pitching? Any fun or creative ways to talk about The Money that have worked well for you?

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How do you decide if a new opportunity, new idea, or customer segment is worth pursuing?

This comes up in every stage of every company!

New ideas trigger a decision point: should we spend time on this?

I like using a bullseye framework to quickly triage the value of a project, idea, or strategy.

Another tactic used by successful entrepreneurs is to make a hypothesis.

Here’s how it works…

Hypothesis Method: 5 Actionable Steps

1. Identify the hypothesis.

Write it down. What is the high level concept you’re testing?

Examples:

I hypothesize that this channel could help us reach more customers.
I hypothesize that our product could also help this customer segment.
I hypothesize this type of internal stakeholder is a more likely buyer.

Writing it down helps you get crystal clear on the next step…

2. Name a successful outcome.

If the hypothesis is correct, how will you know? What do you expect to happen if you’re right?

Identify a benchmark and make it SMART.

Examples:

We will close 2 deals within 2 months through this channel.
We will create $100,000 of pipeline within this customer segment.
We will get over 1000 likes on this social post if the messaging resonates.

The odds of this exact benchmark happening are zero 😁

Results are usually a shade of gray and a judgement call.

BUT — having an idea in your head of what “success” looks like is important. It provides an anchor and accountability.

3. Plan your test.

How will you test the hypothesis?

Examples:

We will do 5 blog posts and 5 social posts targeted to this new market.
We will dedicate 10 hrs/wk of a current SDR to call on this customer segment.
We will send an email campaign to this stakeholder.
We will do 20 customer discovery calls with this new persona.

Here are real life, lightweight examples of authentic demand and product concept tests.

Get specific. Use a priority spreadsheet if needed.

Beware of “doing good stuff” that feels productive but doesn’t quite align to your hypothesis. Time will pass but you won’t be closer to a clear result.

4. Set a deadline.

How long are you willing to test?

Before you start, decide when you will evaluate the test results. This is key for accountability and to avoid “just-one-more-week” syndrome.

Examples:

I will schedule a calendar reminder for 6 weeks out.
I will schedule a meeting with an advisor for the deadline to be a sounding board.  
I will align this with quarterly goals and tracking.
I will evaluate after talking to 25 customers.

5. Analyze the data.  

Arguably the hardest step — was the hypothesis right or wrong? What did you learn?

One challenge is that “data” or “results” are rarely clear cut:

Some customers said x, some said y, some said z.
More deals closed but not as many as we thought.
We got 800 social shares but did not hit our 1000 goal.

Understand and watch out for confirmation bias. Being honest with yourself, even when it’s hard, gets you closer to the right path faster!

Having trouble getting clarity on your hypothesis?

Talk it over with a trusted resource, trust your gut, or come up with a new hypothesis to test!

Top Entrepreneurs Do This

Show me a great entrepreneur and I’ll show you someone who is testing ideas.

Whether intentional or subconscious, top entrepreneurs use the hypothesis method constantly.

They look at data, listen to customers, see what the market tells them, and adjust rapidly.

Identify your hypothesis to quickly and consistently find the signal through the noise!

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Do you use the hypothesis method, either intentionally or subconsciously? How do you know if an idea is worth pursuing?

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