‘Tis the season…to realize you are wildly behind on your 2025 planning. 🤦♀️ Here are 5 key strategies to make annual planning successful (with lots of resources of course)…regardless of how chaotic things are!
Read More‘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!
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.
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.
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
As part of your annual planning…make a plan for accountability!
Pre-schedule goal review meetings
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
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 the holidays????” O’Daily to the rescue! I created a gift guide for all the entrepreneurs (and startup friends)!
Read MoreAre 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:
Forward to loved ones.
Print it, circle fave ideas, leave on kitchen counter.
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. 😉
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!)
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! 😂)
Mug, cross-stitch, t-shirt, or sign with a favorite saying or inside joke. Inspo to get you started:
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.
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 😉
**FREE** The O’Daily in their inbox every week 😉
Group coaching like Scalebound or Glue Club
Masterclass or course/session from their favorite thought leader
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!
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!
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? Yes, please! Price is more than a dollar figure on a webpage. It determines if your business makes money! Here are 10+ resources to make more money starting NOW!
Read MoreRead 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 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!
Use this Gdoc template for customer conversations
Fynn suggests running “willingness-to-pay” conversations at 3 stages:
Pre-product: is this worth building?
Design partners/early users: what customers will pay?
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!
Demo & Value Prop - set the stage
Value Prop Discussion - where do they see most value
Your Relative Value - how does your value compare to other tools they use
Price Metric - fave new term! users, API calls, # of contacts are all price metrics
Packaging Schema - react to example good, better, best packages
Maximum Willingness To Pay - what’s the most you’d pay
Other Factors Influencing The Buyer - get more context
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!
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! 😂
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. 😉
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
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!
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?
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!
Read MoreDo 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!
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.
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!
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!
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!
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?
What worked — what was necessary in the early days — starts to slow you down. 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!
Read MoreIt 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!
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!
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!
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!
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??
What’s the #1 thing on the mind of a software founder?? PRODUCT! (Also: customers, hiring, coffee, selling, cash flow, cap tables, sleep, food, more coffee.) Here are 6 of my favorite ideas to guide you on product building.
Read More🚨ALERT🚨 In Person Event!
Come join me and Christine de Wendel, co-founder and CEO at sundayapp, at Atlanta Tech Village **THIS WEDNESDAY** for a fireside chat. We’ll cover how to find a great idea, fundraising, scaling, and of course, product! 😉
Wed, Nov 13, 12-1:30p | Register here
(and now back to regularly scheduled programming…)
What’s the #1 thing on the mind of a software founder??
PRODUCT!
(Also: customers, hiring, coffee, selling, cash flow, cap tables, sleep, food, more coffee.)
Product is creative, iterative, and there’s so many inputs — customers, investors, engineers, the internet, your own brain!
It can be hard to figure out where to start (or finish!) when it comes to product.
You know the importance of a well-built product and thoughtful roadmap but it’s easier said than done.
Here are 6 of my favorite ideas to guide you on product building.
Different frameworks work better for different companies, founders, or stages.
Pick what feels right for you and share other favorites below! 👇👇
Especially when you’re getting started, I LOVE the question Jon Birdsong asks:
It forces you to:
Focus
Prioritize
Deeply understand your customer
Once you are further along, it’s still a helpful question!
Do you know your next 3 features? What is the value to customers and impact to the business? Does everyone in the company know what they are and why?
The only features allowed on the roadmap will serve 80% of your customers. No one-off features for a fringe (but large) customer.
We followed this religiously at Pardot. We turned down large deals or great logos because they needed one feature…that no one else would use.
This worked especially well because we focused on small and medium business (SMB) customers. A small customer paid $12,000/yr. A large customer paid $36,000/yr.
It gets harder when your small customers are $5,000/yr and large customers are $500,000/yr.
And, if you sell $1M+ contracts, the 80/20 rule probably doesn’t apply. Lootttttsss of custom work at that price point.
Here’s the most important thing to remember:
Building one-off features is always painful.
Always.
Takes longer than you think, you have to maintain it, and it’s never as easy to “repurpose” for another customer as you think.
If you’re small and it’s a really big customer, maybe it keeps the lights on. If you decide to do it, for the love, make 100% sure you have a signed contract for a year or more before you start building things!!!!!
That said, even if you have big customers, 80/20 is always a great framework to keep you focused on adding the most value for most of your customers.
Marco Dell’Olio, CTO and co-founder of Zinnia, said this so well:
We want to have an opinionated product.
Zinnia is a copilot for account executives (AEs), using best practices learned from Lauren Goodell as a top AE at Microsoft and Salesforce. It doesn’t let any rep do any process. Built into the product are certain “opinions” about what good selling looks like.
David Cummings shared similar advice recently (paraphrasing):
Listen to customers, take their feedback, then use your own filter and vision of where the world is going to decide what to build.
A small example:
We never did any direct mail functionality at Pardot. Sending direct mail (aka in-your-mailbox-at-your-house advertising postcards) was often requested by customers and several competitors did it.
We did not. The world was going digital. That was our belief and vision. It was different than others and that was okay. It attracted the right users, kept our product focused, and became part of our thought leadership platform.
A famous Steve Jobs quote which is sorta right.
Customers DO know what their frustrations are.
And you should absolutely be listening to your customers!!!!!!
Solving customer problems = how you make money.
But don’t do exactly what your customers say all the time!
(See also “Have An Opinion”, “80/20 Rule” and “Negative Roadmap.” There’s a theme! 😂)
Customers will kindly and helpfully tell you exactly how to build your product to solve their problem.
These are almost always bad ideas.
And I say this as a well-meaning software customer who has suggested many bad ideas!!!
Your customers are smart and experts at what they do!
But they don’t have the full context and are rarely “product” folks.
What to do?
Dig in to understand what they are trying to accomplish.
Also called the 5 Whys.
Customer: I need a green “Send Email” button right here!
Product: Oh, you want a green “Send Email” button there? Why? What are you trying to accomplish?
Customer: I need to email this chart to my boss.
Product: Interesting. Why’s that?
Customer: She wants to see the data every day.
Product: I see. How does she use the data?
Customer: She compiles it into an ROI analysis and shares with her boss.
Product: Why’s that?
Customer: This product is expensive and we have to show the value. Also, if we don’t export the data daily, we can’t go back and get it.
BOOM.
This customer doesn’t need a send email button. They need better ROI reporting.
A great product person will understand the customer problem — sometimes even better than the customer does — and figure out the most simple, elegant, practical solution. (Billy Hoffman is a genius at this!)
It will solve this customer’s problem but also be designed and implemented to solve other customers’ problems too!
#PROTIP
Usually there’s a handful of customers who DO have really good product ideas. Figure out who they are and stay in touch regularly.
You have a lot of functionality you definitely want to build.
Just as important:
What are you NOT going to build?
Awesome overview of a Negative Roadmap from David Cummings.
Last but not least, here’s a friendly reminder that EVERYTHING is a tradeoff.
Go fast, keep it lean, product won’t be perfect.
High speed, high quality, big price tag.
Beautiful product, small team, takes a long time.
No right or wrong answer. Depends on your market and stage.
Go in eyes wide open and be intentional about what you are choosing.
When in doubt, my rec (for a startup) is speed.
The company with the fastest customer feedback loop has the best chance of building something customers love!
What are your favorite product ideas? What helped you build faster or smarter? Do you use any of these product concepts?
Sharing the cheat codes in startups and life! This is what the O’Daily is all about. I started with 6 things I’ve seen wildly successful folks do over and over again. And I realized…THERE’S MORE!
Read MoreSharing the cheat codes in startups and life!
This is what the O’Daily is all about.
Why should you learn things the hard way when I’ve already done that???? 😂😂😂
I started with 6 things I’ve seen wildly successful folks do over and over again.
And I realized…THERE’S MORE!
Here are 3 more things that highly successful business people do…and now you can too!
For me, this falls into the annoying-but-necessary category.
Don’t hate the player, baby, hate the game!
There is an art to a non-cringey, humblebrag.
Great sales people and CEOs are usually really, really good at a one-line drumroll to make something or someone sound awesome.
(Including themselves. 😉)
In almost every call, meeting, or networking event, you will get asked about yourself.
It’s your chance to establish your credibility, give background, and (ideally!) make someone laugh or lean in for a follow up question.
DO NOT GIVE DISCLAIMERS OR UNDERSELL IT.
The most successful business people have a short, awesome, funny way they describe themselves and their career.
If you ever meet Kara Brown, hers is genius.
Christine de Wendel’s is also excellent.
Mine is…decent. I consulted with an expert (my husband) to improve it.
Sharing as an example, not the ideal. 😉
Less than 10 words: Startup COO turned VC. 7x Ironman. Mom of 2.
One sentence: I’ve been scaling startups for 15 years, as a customer leader and COO, with multiple exits to public companies. (Insert joke about switching to the dark side as an investor.)
And I always say my title!
Yes, of course, there’s a hundred details and caveats. Everyone's career is more than one sentence.
Doesn’t matter. No one cares. They can ask about details later.
It’s like a company pitch. Make it short and easy to remember. Tell the BEST version (no lying though!).
You would never say, “We’re an AI platform that’s doing fine but not great and let me show you every feature and explain the pros/cons for at least 15 minutes.”
Yet that’s sometimes what people do with their personal pitch.
Why don’t people have a personal elevator pitch?
It feels awkward! Egotistical even.
But you are telling your story either way. Make sure it’s the one you want.
Practice, iterate, read the audience, try out new stuff, and find that A+ personal elevator pitch!
I love helping other people succeed.
As COO, team manager, customer success manager, and, now as an investor, if I do my job well, I’m in the background and someone else shines.
Me and Jason Bourne = you’d never know we were there!
I love helping other people succeed, but it poses a challenge (see Personal Elevator Pitch above):
How do I convey that I’m good if the whole point is to make someone else look good? You don’t want to undermine someone and take credit.
I asked someone in a similar role and she shared wisdom that changed my life:
Get the biggest title you can.
Yes, you have to deserve the title. You can’t (often 😉) go from intern to VP Sales in one move.
But when you have a big title, especially in supporting roles, you don’t have to constantly explain your value. The title says it for you.
When “VP of Operations” was proposed as my promotion, I said, “I’d like to be COO.”
“Okay, sounds good,” was the response.
It was that quick, simple, and made all the difference.
BONUS: This can also be used customer-facing. Give your team meaningful titles to provide instant credibility with customers, especially if they are younger or the company is starting out.
“But I don’t like negotiating.”
That’s what I told Adam Blitzer when I shared the job offer I was considering and he asked if I had negotiated.
He told me something that changed my life:
“Always negotiate.”
Then what really blew my mind:
“I don’t like negotiating either.”
Whaaaaa?
Adam was the guy asking for discounts on conference booths, vendor contracts, or brokering a $95M bootstrapped exit.
Adam was the co-founder at Pardot, an executive at Salesforce, is now the Datadog COO.
The dude can negotiate and seemed to enjoy it.
Young, foolish Kathryn thought the only people negotiating were those who loved it.
(And continuing the narrative in my head — those who loved it were mostly men and it came easy to them.)
FALSE.
Negotiating a contract, job offer, business transaction, or anything really — is one of the most meaningful things you can do for yourself and your company.
The stress is high but the time required is small and the impact lasts for months and years.
Top business people ALWAYS negotiate. They expect you to negotiate too.
And — surprise — it gets easier with practice.
Don’t love negotiating? Do it anyway! 😉
What’s your personal elevator pitch?? What other tips have you picked up from successful business leaders? Do you agree with these learnings?
The more you know, the less scary things are. In honor of Halloween, here’s a giant cauldron of tips and strategies with over 20 blogs to navigate the not-so-spooky world of VC and fundraising.
Read MoreWhat’s scarier than passing a motion-activated Halloween decoration on a morning run???
Pitching in front of a Patagonia-wearing horde!
Delving into the murky shadows of fundraising!
Or (gasp!) venture capital investor in the flesh!!!!!
WATCH OUT!!!!
As I remind kids (and myself 😱), the more you know, the less scary things are.
Ditto for investors!
In honor of Halloween, here’s a giant cauldron of tips and strategies with over 20 blogs to navigate the not-so-spooky world of VC and fundraising.
Wellllllcome. (Door creaks.)
How to find, meet, and build a relationship with investors.
6 Simple Ways To Build a Relationship With a VC
Find Your Ideal Investor In 5 Easy Steps
Looking For Funding? Here's 6 Ways To Find It!
First Hand Experience: What To Know About Fundraising With Strategic Investors
How to refine your pitch and fundraising deck.
Show Me The Money: #1 Tip For Pitching Investors
4 Ways To Crush Your TAM/SAM/SOM
How To Talk About Revenue...When You Don't Have Any
6 Strategies To Find Your Perfect, Bite-Sized Pitch
10x Your Elevator Pitch With 4 Words
5 Resources to Help You Nail Your Pitch
Behind-the-scenes insights and advice.
3 Unexpected Fundraising Secrets From a VC
Part 1: 4 Strategies Unicorn Founders Embrace
Part 2: 4 More Strategies That Unicorn Founders Embrace
ICYMI: The What, Why, and How of Building a Billion Dollar Business
4 VC-Approved Tips to Make Your Startup Irresistible
Key Startup Metrics For Each Funding Stage
How VCs Are Approaching Valuations in 2024
The Truth About Fundraising In The Summer (Plus 5 Strategies!)
How to get your head right and play the mental game.
3 Strategies For Establishing Credibility — No Matter Who You Meet
6 Ways To Project Confidence Without Trying
#1 CEO Secret: Everyone Has Imposter Syndrome
6 Habits I’ve Learned From Highly Successful Business Leaders
Top CEOs Are Confident For No Reason
Have a spooooooky investor story? What other fundraising topics seem murky and mysterious? Any venture capital ghosts we can exorcise???
We’re back in 2024 with the most appreciated blog of the year. tl;dr: IT’S TIME TO ORDER CUSTOMER GIFTS!! Here are 3 new customer gift Ideas for startups!
Read MoreWe started in 2022.
I did it again in 2023.
It was so popular…we’re back in 2024 with the most appreciated blog of the year.
tl;dr: IT’S TIME TO ORDER CUSTOMER GIFTS!!
(You’re welcome. Click here to skip jokes and go directly to the how-to guide.)
Bad News: You’re already behind.
Good News: You have time to get started!
If you want to know what the hot new-new is (this guide is from 2022), I still recommend talking to someone cooler than me. You know who I mean. The friend or coworker who knows allllll the trends.
(And please share their recs below! 👇👇)
But I do know 3 cool things and here they are!
Based out of the Atlanta Tech Village, with an amaaaaazing gift box for dudes (and a partnership with another brand that does women gift boxes), my husband got one and it was SO FUN. He loved it, I loved that he loved it, and my kids used the box for a boat/fort/weapon/vehicle. Win all around.
Based in Atlanta with a woman CEO and they have healthy things like fruit??? I am a sucker for these. Delicious, fun, and easy to send. (They have sweet treats mixed in with the fruit 😉). Sure to be a fan favorite in the office.
A personal touch while supporting local startups like you! Check out the P10 Foods list of brands to find awesome Southern brands at nearby stores. Same founders at King of Pops.
For a non-DIY version, Basketry (Louisana-based) and Giften Market (woman-owned, Minnesota-based) both have beautiful and fun options.
Here’s the tea:
And while you’re at it, think about employee holiday gifts too:
Important: If you’re trying to do a company holiday party…DO NOT PASS GO, DO NOT COLLECT $200, GO DIRECTLY TO BOOK A VENUE.
These fill up months ahead.
Or do it #scrappy and have it at someone’s house. Or on a Monday night (best price). Or an AirBnB with no rules about parties. You have options but gotta jump on it!
Any favorite gifts or other recs? What did you do for customers? Any helpful lessons learned??
Save yourself the years of therapy, unending achievements, and exhausting insecurity! Start being confident for no reason. The top CEOs do it too!
Read MoreTop CEOs exude confidence.
Yes, of course. They’re smart and successful. Look at how good they are at <insert what you admire here>.
It’s true for F500 CEOs and the CEO of the hottest startup you know.
Are they confident because they are great CEOs?
Nope.
Here’s the thing:
They acted with confidence BEFORE they were top CEOs.
If you wait for a reason to be confident…it will never arrive.
Because there’s 1,406,596 reasons that other people are better than you.
There’s also 1,406,596 reasons that YOU ARE AWESOME. Right now. Today.
Yep.
Even without achieving whatever it is you think you need to achieve before you can be great.
Because let me tell you…once you get to that official point of greatness, it actually won’t be that great.
You will see another point of greatness!
Just off in the distance…
THAT is the real point of greatness.
That ‘point of greatness’…it’s not really there.
It’s always a little further out.
How do you break the vicious cycle of never-arriving-at-your-greatness?
It’s simple:
Start thinking you’re awesome right now!
Save yourself the years of therapy, unending achievements, and exhausting insecurity!
Start being confident for no reason.
I see you rolling your eyes. (#momvision)
Kathryn, you say, if it was that easy, I would have already done it!
Yes and no.
There is a natural human tendency to want what you don’t have.
And the journey and anticipation of the goal is usually more fun than actually getting there.
You can’t totally override biological wiring from millions of years of evolution.
BUT.
You can start TODAY being a person who interacts in the world with confidence.
Start believing — right this very second — that:
People will take my call and reply to my email
Someone will help me when I need it
I can figure things out
I deserve to be here
I will close deals
And 100 other cheesy, yet effective, thoughts that change how you feel, act, and show up.
People with those beliefs interact with investors differently.
Trust me. I’ve seen it.
They are still polite and socially appropriate but there’s an under current of expectation in their communication that comes through and is very compelling.
If you’re not there quite YET (← “yet” — a word of confidence!), that’s okay.
You’re not alone.
As far as I can tell, most people feel some kind of Imposter Syndrome.
Including top CEOs.
They work hard to overcome it, show up with confidence, and establish credibility.
You too can use their strategies too!
Here are two more that I recently came across:
Say “I’m excited” instead of “I’m nervous” → here’s the research. I recommend Vanessa Van Edwards’ entire TedTalk. I watched twice!
Focus on “the gain” over “the gap” → think about what you’ve made progress in instead of what you have left to achieve. Love this concept (and book!) from Dan Sullivan and Benjamin Hardy, shared by Brad Barrett. I did it in my nightly gratitude journal and — even when I knew it was a trick — it still was magical!
Practice, learning, and pretending are all very effective at building confidence. 😁
You can give yourself permission. Right now. To be confident.
What would happen if you ACTED with the confidence of a top CEO?
What would happen if you saw clearly how awesome you already are?
What would you do, say, ask for, or attract?
It costs nothing but can change everything.
Start today.
For no reason.
Without explanation or justification.
BELIEVE IN YOUR SELF.
And the world will follow your lead. 😉
What is your best tip for projecting confidence? What are the most important insights you’ve learned about doubt, confidence, and success? When do you feel the most confident?
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