The eternal question of startups:

Should I outsource this or hire in-house?

No right or wrong answer and a lot of “it depends.”

ANNOYING, right???!!!!!

But if startups were easy, everyone would do it. 😉

Let’s get into the tradeoffs, considerations, and how to decide the right path forward on your hiring plan!

(BONUS: a few of our favorite “outsource” folks are listed at the end!)

What does in-house and outsource even mean?

In-house and outsource are casual, non-official terms so if you hear someone using them, ask clarifying questions!

Definitions can vary across industries, roles, or companies, but here’s how I’ve seen it often used at startups.

In-house (often) means:

• Hiring a full-time person

Outsource (often) means:

• Hiring a contractor

• Hiring a firm or self-employed individual to provide the service (e.g. recruiting agency, legal services, marketing agency)

Gray area:

• Part-time employee (e.g. someone who is a W2 employee but only works 20 hours per week)

• Fractional executive (e.g. fractional CMO, fractional COO)

Important Legal Thing: 1099 vs W2

Here’s a good overview on the difference between 1099 consultants/contractors and W2 employees — and when you might legally need to hire someone “in-house” even if they are not full time.

Basically, if you want to control when and how someone works, even if they are not full-time, they should be a W2 employee.

Sanity Check

First off, I always like to confirm that you really do need to pay a human for this work.

Can you use AI, software, interns, bartering, or get creative in some other way to keep your startup budget light and flexible?

For the sake of this blog, I’ll assume you explored other options and you DEFINITELY need another human to help.

How do you decide if you should look for a full-time, in-house hire or outsource in some way?

No right answer - lots of tradeoffs!

Here are the top four considerations to evaluate if they should be in-house vs outsourced.

4 In-House vs Outsource Considerations

1. Money

Is this obvious? Hopefully!

Crunch the numbers on the annual cost of a full-time hire vs the cost of an outsourced resource doing the work.

Get a few quotes, do online research to get ballpark salary or per hour numbers, or ask other founders.

Make sure to include the cost of benefits, health insurance, taxes, computers and software, onboarding, and other “hidden” costs of a full-time hire.

Example: Recruiting

Should you hire a in-house recruiter or use an outsource one?

• How many hires are you making this year?

• What will you pay per hire to a recruiter?

• What is typical comp for a full-time in-house recruiter?

• Napkin Math: usually, if you’re planning to hire 1 employee/mo, it’s worth it to hire a recruiter in-house.

2. Work

Hopefully, this, too, is obvious!

What work will this person do?

Write it down! If you can’t write it down, you’re not ready to hire. Put # of hours per week next to each task.

How much work is it?

Is it definitely full-time, maybe full-time, or definitely part-time?

Other considerations:

• Is it steady or cyclical?

• Is this an ongoing need or one-time big lift? (e.g. launching a product or going to a conference)

• Are you running an experiment into a new market or industry? Or is this a validated area?

Example: Legal Services

Should you hire your own in-house lawyer or use someone on a part-time/fractional basis?

• How much is a full-time lawyer salary vs per hour rate? How many hours per month?

• Is there a “busy” time (e.g. end of quarter for contract review, when a large transaction is occurring) or is it always busy?

• Usually, smaller startups keep it outsourced (e.g. a lawyer on retainer for x hrs per month). Larger ones bring it in-house. Especially when they start to get really big bills and find someone they like working with. Come on, lawyer friend, join the company! 😉

3. Incentives

Very important, least often discussed.

How does incentive alignment shift when someone is not on your team?

Examples:

• Lawyers - paid per hour → the longer it takes, the more they make; not incented to be fast and simple; no direct focus on company revenue or customer happiness

• Recruiters - paid per hire → will coach a candidate on what you are looking for, higher salary means higher commission; less incentive for long term fit and salary negotiation

• Engineers - paid per project/hour → happy to build what you say even (especially?) if it increases time or scope; no incentive to push back on speed, priority, or customer utility

HUGE DISCLAIMER:

I know, and you probably do too, many wonderful people in these roles who don’t operate this way!!

They are amazing partners and I often work with these “outsourced” roles and many others with lots of success.

But it’s important to understand where incentives may be different so you can see the tradeoffs or potential friction points and go in with a plan.

There’s also incentive alignments that work to your advantage — your partners want to do a great job so they can continue to win your business and you only pay for work completed or results delivered.

4. Company Culture

A little warm and fuzzy here but there is a certain loyalty and energy that comes from people who are full-time, in-house hires.

Like a marriage compared to a girlfriend or boyfriend, they’re more likely to share improvement feedback, stick through tough times, go above and beyond, and invest in people and relationships within the company. Not to mention, get drunk at the holiday party, create a crazy tradition, or other key team-bonding behaviors. 😂

Of course, every founder has different preferences or goals. Some love the flexibility of contractors or like having no full-time hires.

And, there’s tons of amazing contractors and consultants who care deeply. Some even work with specific companies for years and years.

But the nature of outsourced work is that it’s less likely they are investing in your company culture.

There may be certain roles or people where the spreadsheet says to outsource but you bring in-house because of the positive impact on culture.

Or maybe a better way to put it is: every person you work with — in-house or outsourced— is shaping your company culture.

Do you like how it’s shaping up? 😉

Looking For Recs? A Few Favorite “Outsource” Folks

So many amazing people out there! Please list your go-to recommendations in the comments 👇👇👇

Here’s a plug people for we work with at Atlanta Ventures!

• Evie Lutz of Confetti Social - brilliant and lovely to work with

• Carver Creative - fantastic team for all marketing activities

• Hilton Thompson of Folks Events - our go-to for happy hours and big events

• Skip Blankley of Juxt Media - video marketing and podcast everything

• Virgil V - our WebFlow and other martech guru

• The many, many interns - love y’all, best talent-per-dollar on the market

• Our amazing, kind lawyer who I won’t mention by name because he not taking new clients but he sometimes reads this blog, so Hi W!

What are your biggest hiring questions or challenges? Any learnings related to in-house hiring vs outsourcing? Who are your favorite contractors or consultants to work with??

Building a big company? Hard but possible.

Staying healthy while building a big company? Also hard but possible 😉

Your company wants and needs you at your healthiest.

There are real business benefits to a healthy founder:

• more mental clarity and sharpness

• better emotional regulation during startup highs and lows

• energy for travel, customers, and emergencies

• rarely out sick

• endurance for the startup journey (a 10 year overnight success 😂)

• happiness! which translates to confidence, optimism, and making shit happen

It can be hard to carve out time for an important-but-not-urgent thing like your health.

That’s why I have spent 15+ years figuring out how to move, eat, and rest in the most time and cost efficient ways (including 7 Ironmans while scaling startups).

HERE ARE THE CHEAT CODES.

These are the top health-related O’Daily blogs with allllllll the tips, recipes, strategies, tiny habits, daily schedules that make it possible to infuse health into a chaotic schedule.

No gimmicks. No big price tags. Simple, actionable, manageable things that I’ve done, healthy founders do, and you can too!

TL;DR: Top 3 Things

Don’t have time to even read this article? Here are my top 3 recommendations in priority order.

1. Move more.

Walking meetings, a walking pad at your desk (<$200 on Amazon!), take the stairs, park far away and walk. Exercise is the most important factor in longevity - 3-4x more important than what you eat. Check out the eye-opening analysis in Peter Attia’s Outlive.

2. Eat more vegetables.

Change nothing else about your diet except adding vegetables wherever you can. More fiber, more water, more nutrients. Humans love adding and hate restricting so this mindset and habit is easier than other dietary changes.

3. Better sleep.

If you missed the memo on sleep, it makes you smarter, healthier, better looking, and happier with no other changes to your life.

I say “better” not “more” for a reason. “More” is ideal but if that’s not possible, make it high quality. Eye covers, cool temps, blue light glasses, morning sunshine, and avoiding late night caffeine, snacks or booze, can make a huge difference in quality with no additional time. (Pick one change to start!)

Ultimate Guide: Top 7 Blogs For Healthy Habits

6 Tiny Healthy Habits No Matter How Busy You Are

Pick 1. They are easy. I promise you can do at least 1 even if you are working 100 hrs/wk. PROMISE.

5 Ways To Eat Healthy When You’re Building a Company

The most important strategies I’ve used again and again during every stage of startup and life.

5 Fast, Healthy Lunches For Busy Startup Days

My favorite lunches — brown bag or going out. Use as your weekly meal plan.

Ditching Processed Food 101 for Exhausted Founders

Our slow journey to more (easy!) homemade foods with recipes, examples, and the list of foods we still buy pre-made.

5 Healthiest Fast Food Picks For Busy Founders (& Their Families!)

I share my go-to spots with healthy options that are easy to find, especially when traveling.

A Simple 3-Step Guide To Building Lifelong Habits

How to test possible new habits and make small, sustainable changes instead of overhauls. (I am guilty of many failed overhauls!)

Want To Be the Best? First, You Need to Be the Worst

Your friendly reminder that all new things are hard at first. That doesn’t mean it’s not working. It will get easier.

Or as my husband says, the first step of a new habit…is when you realize you forgot to do your new habit. Forgetting is the first step to remembering!

One Small Thing

I’m a HUGE believer that daily, sustainable habits beat occasional, heroic efforts.

True for health and building startups 😉

My favorite recent example that I learned from this podcast:

Walking 5 minutes every half-hour is better than walking an hour at the gym followed by sitting all day. (And the reason I got a walking pad for 2025!)

This research from Microsoft shows small breaks have brain power benefits too.

Don’t have 5 minutes? Do 10 squats. Refill your water bottle. Stretch in your chair. Tap your foot and annoy everyone around you!

Your small daily habit will compound over time. Just like your startup!

What’s the #1 healthy habit you’re tackling in 2025? How do you stay healthy while building? Any favorite tips, recipes, or tools? What’s the hardest thing to make time for as a founder?

Remember when we talked about not being the bottleneck?

And how important it is for the company to be able to move fast?

But here we are…2 months after I gave you the keys to the speed castle, and you still feel totally bogged down.

What’s going on???

Why are you still getting in your own way?

Let’s take a look at 4 common ways a founder or startup leader might be unintentionally slowing things down…and how to fix it!

1. Seagull Management

What’s seagull management, you ask?

1. My favorite business term.

2. My least favorite business practice.

3. Defined as: swooping in and shitting all over everything!

The key to a successful anti-bottleneck campaign is you.

You cannot delegate and second guess every decision.

You cannot hand off a project and then redo everyone’s hard work at the very end.

If there is something absolutely awful and it’s very important, then by all means, get in and fix it.

(Even better: use it as a teaching opportunity or improve and clarify the process!)

If it’s simply not how you would do it or it’s 90% as good as what you would have done, make like Elsa and spend energy on more important things.

Remember: you made mistakes along the way also! 😉

2. One-and-Done Mindset

Congratulations!

You audited, delegated, documented, and let the people around you succeed!

Sit back, relax, and prepare for…your problems to happen all over again.

Wait whaaaaaa?

No productivity strategy is set-it-and-forget-it, especially not in a fast-moving startup.

You will forever be in your own way if you delegate, optimize, or streamline once and expect to be done.

You *MUST* revisit your priorities, time allocation, and what you’re delegating (or not) on a regular basis!

3. The Fun Thing

Learning constantly can be really energizing. But it can also be really hard.

You suck. A lot.

All founders —regardless of stage and success level — are fighting imposter syndrome and hoping they grow fast enough to keep up with their company.

When everything feels hard, you desperately want to do something easy:

“Let me jump back in and code. I know I’m good at that. It’s way easier than selling enterprise deals and I like feeling that I’m good at something for a change.

It’s human nature to do things you like and are good at.

There’s also an aspect of fun.

Most founders like new, fun, innovative things. Doing big company things like annual planning or board meetings can feel booooorrrrring.

But hurts the company if the founder is distracted.

We’ve all seen it.

The founder that goes down a random rabbit hole of “cool new technology,” codes an unneeded feature over the weekend, or rides-along on a sales deal to show they “still got it.”

Listen, I’m all for productive procrastination.😉

But watch out for too many “fun” things that don’t help the company!

4. Helping Too Much

Founders genuinely love their team and want to create a great work environment.

If things are insanely busy or someone is struggling, a founder’s natural inclination is to jump in and help!

You set the example that no job is too small.

You roll up your sleeves to get things done no matter what.

I love this. To a point.

Here’s when it becomes problematic…

When you, as the founder and CEO, are not getting the most important things done — that only YOU can do.

It’s often referred to as “the best and highest use of your time.”

If you’re busy answering support tickets, you’re not talking to investors or doing strategy sessions with the largest customers.

And no one can do that but YOU!

You think you’re helping but often your team wondering:

Why are they jumping in on support tickets? I want them to be raising money! I can handle the tickets but I can’t fill the coffers.

The other downside — “helping” everyone can put you on the verge of burnout or make you annoyed, tired and sluggish. Everyone wants their CEO to be firing on all cylinders!

The Fix

You know you’re the problem. What do you do next???

1. Knowing is half the battle! Sounds silly but often people don’t realize they are doing these things or the “why” behind them. Once they read this blog (hint hint) or someone points it out, they have an “ah-ha” moment.

2. Stress makes it worse. When I’m stressed, I hyper-focus on details. I often miss an obvious solution because I’m too deep in the weeds. Since I know I do this, I can combat it. I force myself to zoom out, or ask a trusted “big picture” friend to see what I’m missing.

3. Reframe it. Rewrite the narrative from “my company needs me” to “the best CEOs give their team freedom” and “the fastest way to exponential growth is to get out of the way.” Your measure of success evolves. When things run smoothly without you, it’s not a threat to your self-worth, it’s a huge win!

4. Enlist an ally. Is there someone at work who can be honest with you when you’re getting in your own way? Point out your seagull management or procrastination? Ask them to tell you if you’re falling into old habits. Clarify when and how you want them to communicate it.

5. Hire a coach. Or join a peer/founder accountability group. The structure, strategies, accountability, and coaching can be transformational. Just ask other CEOs.

Have you gotten in your own way or become the bottleneck? How did you fix it? Have you ever done the fun thing instead of the hard, productive thing? (I have! 🙋‍♀️)

Welcome to your 2024 O’Daily Wrapped! 🎉

If you didn’t read every post (I only managed to because I wrote them 😂), no worries!

Here are the greatest hits for efficiency and light holiday reading to wrap up 2024!

If you want more advice OR fewer words in 2025, come hang out with me on LinkedIn or Instagram! 😉

1. Are You The Bottleneck Founder? 4 Ways To Get Out Of Your Team's Way!

For founders who want to empower their team…without micromanaging.

2. 10 Pricing Resources To Boost Your Startup's Revenue

Make 2025 the year to unlock your startup's earning potential. Expert tools and tips from Fynn Glover.

3. Not Sure What to Build? 6 Tried-and-True Product Strategies for Startups

Tested strategies to ensure your product aligns with customer needs and market gaps.

4. The Kind of Leaders Who Thrive in Startups

Here’s a list of qualities I often see in top startup employees who move up quickly!

5. 6 Habits I’ve Learned From Highly Successful Business Leaders

Some things that I’ve learned from years of being “at the table” with top CEOs, founders, investors, and executives.

6. 7 Events Every Atlanta-preneur Needs To Know About

The 2024 dates for these events have passed, but many of these events will be back this year. Stay tuned…might just have to post another version for 2025.

7. The Reality of Startups — Tech News Won’t Tell You This

Learn more about the natural bias in what, how, and when startups share news about themselves!

8. Key Startup Metrics For Each Funding Stage

An overview of typical investor metrics or evaluation criteria for each stage of early investment!

9. 5 Free & Low-Cost Ways Startups Can (& Should!) Support New Parents

Parental leave at startups — how to do it right even when teams are small and budgets are tight.

10. 10 Free & Low-Cost Resources for Women Founders (ATL & Beyond)

Looking to get started in tech, looking for community, raising money, or scaling to the next stage?! Check these out!

What topics or posts were most helpful? What should the O’Daily --start, stop, or continue-- in 2025??

The most important blog of the year. It’s the most fool-proof strategy for a great 2025.

TAKE A BREAK OVER THE HOLIDAYS.

If you haven’t seen it lately, here’s my favorite quote about startup performance:

Idk who needs this but I’ve seen a few startups fail because of founder burn out. I haven’t seen any startups fail because a founder took a couple days off.

Thank you, Alex Friedman!!

Even if you are still chasing down deals, no one — LITERALLY NO ONE — is going to sign a contract on Christmas Day or New Year’s Day so take advantage and unplug for a hot minute.

Being refreshed, rested, and your best self is KEY to dominating 2025!

You’ll probably also have an amazing business unlock while you’re whipping up eggnog or lighting the menorah. Let your subconscious do its thing!

Happy holidays from the O’Days (O’Dailys? 😉).

May we all have a crazy uncle who jumps into the family photo this holiday season! ❤️😂

‘Tis the season…

…to realize you are wildly behind on your 2025 planning. 🤦‍♀️🤦‍♀️🤦‍♀️

If you have already started on 2025 planning, CONGRATS!

You are ahead of 99% of startups everywhere.

If you’ve been focused on:

• Hitting your 2024 and Q4 sales goals

• Putting out customer fires

• Closing out your funding round before everyone is OOO

• Spreading holiday cheer for customers, employees, and founders

…totally normal and it’s not too late to be ready for 2025!

Here are 5 key strategies to make annual planning successful (with lots of resources of course)…regardless of how chaotic things are!

1. Start with wins!

Do not pass go. Do not collect $200.

Go directly to…

Make a list of your 2024 wins!

You can do this:

• Personally

• Professionally

• For your company

• As a team

• As a family

(My husband and I do this and it’s incredible to see how much you do — and forget you’ve done — in a year.)

It’s unlikely that you hit every goal.

But you probably did a lot of great stuff and made a ton of progress.

THAT is the energy you want to bring into the new year.

Momentum, improvement, excitement.

Start by focusing on the GAIN not the GAP.

PROTIP: Look at your calendar to recall highlights or start with things you’re grateful for.

2. Include self reflection.

Startups are a reflection of their founder.

You perform, the company follows.

Your growth is intertwined with company growth.

• What did you do well?

• Where do you need to improve?

• Where are you the bottleneck?

• Are you showing up as your best self?

• Any personal or individual goals that relate to company goals?

PROTIP: Sahil Bloom has a great Personal Annual Review. I also do his Monthly Audit (calendar reminder with the questions) and love it.

3. Keep it simple.

What is better — OKRs or a company scorecard? Should you follow the Entrepreneurial Operating System or a One Page Strategic Plan?

The single best framework in the whole world is…

(drumroll)

THE ONE YOU WILL FOLLOW.

Annual plans are like exercise.

All exercise is good for you…if you do it.

The best type of exercise is the one you will actually do!

Don’t get stuck in an internet (or internal) debate over nuances.

Pick something that feels easy, makes sense to you, and works for your stage and company size.

You will improve and get more sophisticated as you build the planning muscle.

Start simple!

PROTIP: Need a starting place? 5 Simple Tools For Annual Planning

4. Make a follow up plan.

As part of your annual planning…make a plan for accountability!

• Pre-schedule goal review meetings

• Hire a coach

• Block time on your calendar for a key project

• Make changes in the physical environment (e.g. rearrange desks to further collaboration, put up a sign that you see daily)

• Set up a recurring meeting, alert, or activity related to a goal

PROTIP: More ideas here → 5 Strategies For Annual Planning Success Despite Startup Chaos

5. When in doubt, less.

Now, look at everything you planned and cut 50%.

Joking, but not really.

The biggest risk to your goals is that you have too many.

The biggest risk to your company is being spread too thin (with time and money) to make real progress.

I love this question from Tim Ferriss:

Which of these items - if accomplished - would make everything else easier or irrelevant?

If I train for a running race, I go to bed earlier and eat healthier.

If you find a great CMO, the other marketing projects are handled.

Focus on the 1 thing that solves everything else!

PROTIP: Use this priority framework to get super clear on your highest value initiatives.

What are your favorite annual planning strategies? What frameworks or tips have worked for you??

Are you frantically trying to close end-of-year deals while your well-intentioned loved ones are asking:

“What do you want for Christmas/Hanukah/Kwanza/Festivus????”

Or maybe they need help and you’re too busy prepping for the January launch to scatter hints all over the house.

O’Daily to the rescue!

How To Use This Gift Guide:

1. Forward to loved ones.

2. Print it, circle fave ideas, leave on kitchen counter.

3. Buy it for yourself. You’ve earned it!

BONUS: many of these suggestions are startups themselves — founders I know, portfolio companies, or innovative tech products. Feel good supporting other founders!

Reminder: customer and employee gifts work great for founders too. 😉

1. Gift of Time

Time is the most valuable resource at a startup. How can you give a founder a few hours back?

• Cookonnect - a real chef comes to your house and preps meals for the week

• Duckbill - virtual personal assistant for $100/mo

• MyPanda - on-demand in-person help (e.g. laundry, organizing, party prep)

• Accomplished App - subscription “house manager” service

• Uber - 1 week of “car service” for that work commute

• Styling service like Fashivly or TheStyleLiz — or fashion subscription like Stitch Fix or Nuuly (get a referral code from a friend for a discount!)

• House cleaning

• Zinnia or other co-pilot tool that you’ve vetted or had recommended! Sometimes finding a good option is the hardest part.

• Give them a “coupon” for a helpful or time-consuming task

(Anyone else gift their parents a LOT of coupons over the years? 😂 IOU a car vacuuming, Mom!)

2. Gift of Health

Feeling good is priceless. Help a founder optimize their performance with tools and strategies for health.

• Whoop - track sleep, activity, recovery, habits. I LOVE mine. It’s helped me get more and better sleep and provides daily accountability.

• Sensate - vagus nerve stimulator. My HRV increased 10-15%. If you don’t know wtf I’m talking about, this is not for you. h/t Andrew McConnell of Alively for the rec!

• Reframe App - quit or cut back on drinking

• Cub App - ADHD support

• AG1 - my go-to health drink. Multivitamin, probiotics, prebiotics, veggie powders in a filling drink with travel packs. It doesn’t replace vegetables and good habits but sure helps me feel good during crazy weeks.

• Package of sessions with a trainer, physical therapist, fave yoga studio, or Peloton app for at-home efficiency

Alively is another great spot for wellness gift ideas. I have discount codes for Whoop, Sensate, AG1 if you need them. (Thank you, referral programs! 😂)

3. Gift of Humor

• Mug, cross-stitch, t-shirt, or sign with a favorite saying or inside joke. Inspo to get you started:

  • Get Shit Done

  • I became the CEO my parents wanted me to marry

• AI image of them on the cover of Forbes or other “making it” moment

• Share any BigTimeAdulting or CorporateNatalie video. They are hilarious and free. Laughter is a great gift.

4. Gift of Connection

• Zest - fun app for couples to stay connected (even when traveling or busy) with daily question + date ideas!

• Set up a regular time for your founder to spend with friends or a partner (e.g. hire a sitter, block it on their calendar, coordinate with the friends)

• Frame an amazing photo (metal print and canvas are great too) for their desk

• Daily calendar of family or company photos

• Membership to Atlanta Tech Village, Switchyards, The Lola, Intown Golf Club, or The Perlant 😉

5. Gift of Learning

• **FREE** The O’Daily in their inbox every week 😉

• A great book (get started here and here)

• Group coaching like Scalebound or Glue Club

• Masterclass or course/session from their favorite thought leader

• Executive coaching

6. Gift of “Founder Survival Kit”

Simple, fun, and thoughtful. Add your own touches!

• Gift card to their favorite coffee shop (like Kula, Spiller Park, Con Leche, or Opo!)

• Healthy, hearty snacks to keep at the office

• Charging brick, extra laptop charger, wired earphones

• Stain removal pen, mints, gum, dry shampoo

• Mini champagne bottle for those impromptu celebrations!

7. Gift of Rest

Last but definitely not least…

Sometimes the best gift is the permission (or forcing function) to take time off.

In one of my fave 80s classics, What About Bob, Dr. Marvin gives Bob a prescription to take a break from his problems.

Follow Dr. Marvin’s lead — give your founder a break from their startup!

• Send THIS TWEET (or this blog) to set the stage

• Plan a day in nature or without a phone

• Brainstorm and implement a new tradition

• Massage, spa day, golf outing, wellness retreat

• Trip with no cell service (e.g. Postcard Cabins, camping)

• Roots App - use your phone more intentionally (or get a timed lock box)

• Ask them what would help them reset, rest, and recharge!

Want more?

Lutely and Wirecutter are my go-to for gift ideas!

What is the best gift you’ve received?? What other startup brands should people know about this holiday season? Other recs for founder gifts?

Read one blog and become a pricing expert?

That’s my goal for you today!

Price is more than a dollar figure on a webpage.

It determines if your business makes money!

Pricing is all about confidence in what you are building and objectively understanding your value.

But the majority of founders build something without understanding what and if people will pay for it. What does your market think about your value???

Pricing is hard, not intuitive, rarely taught or discussed, and often becomes a fingers-crossed number on a sales presentation!

That ends today.

We had an amazing Masterclass-level webinar with Fynn Glover of Schematic where he walked through an 8 step process to assess a customer’s “willingness-to-pay.”

It’s a process used by top (read: expensive) pricing strategy consultants — now available to you via GDoc, webinar recording, and slide deck!

I’ll share an overview of Fynn’s webinar, 2 great pricing podcasts, plus some of my own real life stories about startup pricing.

(Expert tools would have saved us months of bad pricing and made us way more money. 🙃😉🥴)

Buckle up and prepare to rake in the dollars!

Here are 10+ resources to make more money starting meow!

Willingness-To-Pay: Overview

Willingness-To-Pay is a framework for figuring out your value to customers and how to price correctly. You can learn more in one intentional 30 minute call than months of tweaking your pricing page!

• Mastering Willingness-To-Pay Conversations Slide Deck

• Webinar Recording

• Use this Gdoc template for customer conversations

Willingness-To-Pay: Timing

Fynn suggests running “willingness-to-pay” conversations at 3 stages:

1. Pre-product: is this worth building?

2. Design partners/early users: what customers will pay?

3. Post-product market fit (Seed or Series A-ish): does price align with value?

Pricing will evolve over time. Build the muscle of revisiting pricing regularly and plan to iterate!

8 Steps of Willingness-To-Pay Conversations

1. Demo & Value Prop - set the stage

2. Value Prop Discussion - where do they see most value

3. Your Relative Value - how does your value compare to other tools they use

4. Price Metric - fave new term! users, API calls, # of contacts are all price metrics

5. Packaging Schema - react to example good, better, best packages

6. Maximum Willingness To Pay - what’s the most you’d pay

7. Other Factors Influencing The Buyer - get more context

8. Closing Feedback - thank them and ask for feedback on the process

Want more? Get the specific questions to ask and context on each step in the webinar recording and slide deck.

Even a grizzled startup veteran like myself learned some awesome new strategies and questions. I’m coming at you with a relative value question soon!

Willingness-To-Pay: Key Insights & Reminders

Some favorite takeaways:

• Pricing is an emotional conversation. It can be hard on both sides.

• Get comfortable in silence. Let customers really think and reflect.

• Avoid founder charisma. You’re searching for objective truth. The bigger the company gets, the more founders removed from this process.

• Willingness-to-pay is not customer discovery or a sales tool. Do this after you “Mom Test” and run real life experiments.

Reminder from Kathryn: When in doubt, launch and make people pay something. Don’t let “must run willingness-to-pay process and have perfect pricing” become a reason to not ship the thing into the world!

It’s a tool, not a delay tactic.

As you’ll see in my stories👇, companies can be successful even with bad pricing! 😂

Real Life Pricing Stories & Lessons

Straight from the startup trenches! Supplement your Willingness-To-Pay process with tactical tips like, retire old pricing, opt for simplicity to start, and make sure it will cost IBM $1M to buy your product. 😉

• Real Life Pricing Strategy: A Pardot Case Study

• 4 Game-Changing Pricing Tips From Fortune 500 Strategists

• The Price Is Right! 4 Questions To Ask For Perfect Pricing

• 3 Strategies To Analyze Your Pricing Effectiveness

• 6 Hilarious But True Pricing Stories

• 3 Questions To Nail Your Expansion Strategy

2 Recommended Pricing Podcasts

Get even more expert advice!

1) Invest Like the Best: The DNA of Software Companies with Miles Grimshaw

• Hear the story of Segment’s pricing evolution

• #1 rec from Fynn

2) Monetizing SaaS: Lessons from SaaS Operators

• 50+ episodes, ~30 minutes each from real folks who built and monetized great products

• Hosted by Fynn

Schematic & Sales Tip

Fynn didn’t mention his product a single time on the webinar.

I will though!

(If your investor can’t talk you up, who can??)

If you don't want your engineers to work on pricing and billing, and want your GTM founders to fully control pricing and packaging without code changes → check out what Schematic is building!

P.S. I love that the webinar was 100% educational and not a pitch. Everyone expects you to plug your product so when you don’t, it builds curiosity and goodwill. I’ve seen other founders do the same thing with similar results!

Want More?

Fynn offered more pricing deep dive sessions! Shoot him a LinkedIn message if you’re interested.

• Pricing AI Products - 6 AI pricing models with pros and cons of each

• Pricing 102 - Determining your price elasticity, power, and sensitivity

• Packaging 102 - Determining leader, filler, killer features, and add-ons

• Negotiation - How to successfully negotiate pricing for enterprise deals

• Anatomy of the Pricing Page - How do drive conversion from your pricing page

What’s been your most helpful pricing insight or advice? Did you attend Fynn’s webinar? What was your favorite takeaway? Have you run “Willingness-To-Pay” exercises before?

Do you have favorite holiday traditions?

Me too!

Before Thanksgiving dinner, my family will climb Stone Mountain (~1mi hike) and stop halfway up for our annual arm wrestling contest.

We started as kids and continued into adulthood.

Over the years, the group has expanded with spouses and grandkids. The arm wrestling championship has changed hands (arms?) many times.

It is SO FUN to return to the tradition year after year regardless of how much the rest of my life changes. It’s a combo of good memories and regularly making new ones!

I feel the same way about my morning cup of tea. In the craziness of work, kids, training, life…I love a micro-habit (and caffeine 😂) to anchor the day.

How touching, you say.

BUT HOW DOES THIS RELATE TO STARTUPS, KATHRYN????

**transition to business relevance**

In a world of constant change, are there fun traditions or micro-habits at your company???

Traditions doesn’t mean traditional or even holiday-related. It’s about ritual, routine, and small moments of joy sprinkled into the chaos.

When I think back on my favorite startup (and life!) moments, the traditions stand out!

How To Build Startup Traditions

1. There’s No “Right” Tradition

They can be simple, zany, sweet, or funny. What matches the vibe of your team? What feels authentic?

Something you, the founder, are into is a natural fit. Your enthusiasm is contagious.

2. Be Intentional

Sometimes a tradition springs up organically. You can also curate them by trying different stuff and see what sticks. Be on the lookout for something with “tradition potential” that the team is already enjoying!

3. Grow With The Company

Tradition or ritual, by definition, mean “recurring” — which is hard since startups move and grow quickly.

Your traditions may not look the same as you scale, but the spirit will stick even if the details evolve. The memories and goodwill will endure.

A company-wide end-of-quarter potluck may turn into a department-specific event or a catered one. Or, maybe it will be the most epic 5000-person potluck and you rent a stadium to hold all the casseroles and lasagnas!

Startup Traditions In The Wild

Some examples that I recall fondly:

• Friday team lunch with pizza (families invited)

• Holiday gift exchange (draw names, $10 limit)

• Paper plate awards

• Impromptu happy hour at the local dive bar patio on nice days

• Peer-to-peer award at the monthly all-hands (funny trophy or swag)

• Decorating someone’s desk on their birthday

• Daily stand up meeting

• Creating Slack emojis of teammates’ faces or representing core values

• Friendsgiving potluck

• Team photos in costume

• Sending out an email with meme or joke (or limerick - s/o Jennifer Betowt!) when a deal closes

• Ringing the gong on won deals

• Celebrating revenue milestones with big parties

• Company field day and/or picnic

And stories I’ve heard from others:

• Wearing swimsuits and floaties to jump into the retention pond in front of the office building when a big deal closed

• Personalized bobblehead doll on 3 year work anniversary

• Who can wear the most company swag contest/day

You’ll notice the examples I mentioned (exception: parties) are extremely low cost or free.

You don’t need big money to make big memories.

A little bit of time, energy, and attention can have a lasting impact!

A Holiday Week

Happy (American) Thanksgiving and hope you are making awesome memories!

If you are an e-commerce company or retail brand, sending good thoughts on Black Friday/Cyber Monday!

My favorite reminder for holidays, trips, snafus, big events — it’s either a great time or a great story. A win either way! 😂

What are your favorite holiday or startup traditions? What’s the craziest tradition you’ve come across?? Do you have traditions at your startup yet? Did you create them or did they evolve organically?

It happens to every startup.

What worked — what was necessary in the early days — starts to slow you down.

In the beginning, the founder:

• approves everything

• attends every meeting

• weighs in on product decisions

• closes deals

• replies to customers

• leads presentations

• trains new hires

• manages every team member

• aka does everything!!!!

But when you grow (yay!), if the founder is still doing these things, it becomes a bottleneck.

It happens slowly, a little at a time.

Then one day, you realize — you are the problem.

Your team is waiting on you.

You are bogged down, guilty, and behind. You’re in meetings all day and can’t catch up.

Speed is your startup advantage and you can’t leverage it!

How do you get yourself out of the middle and your team unstuck?

Here are 4 steps to resume startup hyperspeed and save your sanity!

1. Audit Your Time

Start with your inbox, calendar, and messaging apps.

• Where are you spending time?

• What decisions are being sent for your approval?

• What meetings are you attending?

Take a step back and ask:

• What should I be working on?

• What do I no longer need to be involved in?

• Who can handle more responsibility?

Here is a detailed list of 5 areas to audit.

You will usually immediately identify several things that you can hand off or edit by spending 30 minutes thinking it through!

2. Clarify Approvals and Decision Making

Once you realize that you can and should delegate, how do you do it?

You’re welcome: The Only Framework You Need to Delegate Like a Pro

I literally LOVE EVERYTHING ABOUT THE DECISION TREE FRAMEWORK.

But if I had to choose:

Clear language for yourself and your team on when/how to tell you about decisions and actions.

In the early days of Pardot, I pinged our COO every day with several questions about pricing or discounts. After a month or two, he said:

I trust you to make these decisions. Do what you think is best. Only run it by me if it’s more than $1000.

Boom. The approvals needed dropped from 15 per week to 1.

Estimated time savings = 1 hour per week.

Now, do that for 10 more small things that are bogging you down!

3. Create Documentation

The example above worked because I was trained through many scenarios. I got a feel for the “why” behind pricing and contract decisions.

Want to skip a step?

Start writing shit down!

Make some guidelines, put together training videos or presentations, and document institutional knowledge.

Guess what? You don’t even have to be the one to do this!

Repeat after me:

I will show you how I do this. Can you take notes and turn it into documentation as part of the learning process?

Or

I created a Loom video to explain what I do. Can you please add this to <Slack channel, Google Drive, Notion, whatever is your Wiki/Knowledge Base tool of choice> and share with others?

Look at you. You created documentation on your first try!

4. Say No, Prioritize, Avoid Meetings

Getting even more tactical — here are common areas that can cause recurring bottlenecks:

• Struggling to say no → 4 Fresh Ways To Say No and Still Be Polite

• Losing sight of what matters → Prioritize Yourself Out Of Chaos With A Simple Spreadsheet...Here's How

• Too many meetings → 5 Strategies For Fewer Meetings & More Time

Fun fact: these are related!

When you know your priorities, it’s easier to say no to things including meetings!

Boom. Bottleneck busted!

Have you ever been the bottleneck? How did you fix it? Any other tips??