Startups for the Rest of Us Notes 2021

Episode 530 | Making Development Decisions, Regrets about Selling, and More Listener Questions (with Derrick Reimer)
Date: 2021-01-05

Someone should be in the leadership position on what the core values are and what types of technologies to use.

It really helps to establish some guiding principles (for picking technology).

If you are going to use a cutting-edge library, know that is a risk.

In the beginning you have one to two product people (making product decisions).

Scaling is a skillset.

There is always a way more money gets you there faster.

The way to get away from platform risk is to build for a bunch of platforms.

Episode 531 | How a Non-Technical Founder Grew Past $20k MRR
Date: 2021-01-12

Give the value to the company that your time should.

When you are in a space that is reputation based, you have to have something good that shows you know what you are talking about.

You can own multiple businesses at once but you can’t grow multiple businesses at once.

Create content focused towards your audience.

Really successful, big companies talk in years (rather than months). Slow down your pace.

Episode 532 | The Art of Selling Your Business with John Warrillow
Date: 2021-01-19

Book: The Art of Selling Your Business

Private equity groups run on big debt.

When the best time to sell is when someone makes you an offer because you have negotiating leverage.

A prop deal is a recipe for you selling your business for less than it is worth.

There is no harm in having a conversation with a strategic acquirer. Arm yourself with a bunch of open-ended “What?” questions.

The reason you use “What?” questions is that they are open-ended and force an answer.

Don’t give up too much information. Information in an M&A process is valuable.

Get an NDA before you (disclose) MRR.

If you can get your earn out tied to something other than earnings then you have a bit more control.

Episode 533: Life Profitability After Two Exits (with Adii Pienaar)
Date: 2021-01-26

Book: Life Profitability

In 2021 going forward we need an augmented version of capitalism.

Building a business is really, really hard.

We don’t work to live and we don’t live to work when work is always a part of life.

Half of being an entrepreneur is managing your own psychology.

Stay in mindfulness. Be aware of when energies change.

Episode 534 | A $4M Exit with Josh Pigford of Baremetrics
Date: 2021-02-02

When you are a product person building features is the way to get out of plateaus. Marketing can help too.

Repositioning can lead to huge growth.

Most investors don’t actually need that much deal flow because they are giving way money.

Validation is not 100%.

Episode 535 | A Bluetick Update with Mike Taber
Date: 2021-02-09

Having two people working on something allows for so much more bandwidth especially if their skillsets are not the same.

We all want things to move faster than they do.

Oftentimes the calculus we have to do as entrepreneurs is if investing this time is worth the potential upside.

Appsumo deals are good for your app if they are low support and low per-user cost.

Episode 536 | A Few Things I Learned in 2020 (A Rob Solo Adventure)
Date: 2021-02-16

(Our personal stresses) compared to other things happening in the world are just not that important.

Doing things in public creates opportunity.

If you aren’t working hard you will never get lucky.

Episode 537 | On Launching, Funding, and Growth with Serial SaaS Founder Rand Fishkin
Date: 2021-02-23

Book: Lost and Founder

What you really want for a healthy economy is a lot of small to medium sized businesses.

Don’t focus on growth at all costs above anything else.

The blog articles are the meat. The blog is the hub. (Social media) is the amplification.

Episode 538 | When to Sunset a Product, Enterprise Security Assessments, Lifetime Deals, and More Listener Questions
Date: 2021-03-02

Usually entrepreneurs want to do too many things and have shiny object syndrome.

A lot of people are anchored to their own price.

Episode 539 | Post-Exit Life, Writing Six Books, and Brewing Beer with Dan Norris
Date: 2021-03-09

(Podcast listeners) tend to be more engaged than with written content.

It is not good to start a software business if you are not a developer.

Brand, story, content, and community.

It is hard to build something into the seven figure run rate without having a brand and community.

If you are going to be a founder you have to find some way to market a business that works.

Growth is expensive.

Episode 540 | Bootstrapper News. Twitter Spaces, Closing, Shopify, and More
Date: 2021-03-16

An acquirer will not pay the same multiple if there is platform risk.

LinkedIn has become the de facto online resume service.

Episode 541 | Faster Horses & Product Myths, Life-changing Money, Dual Funnels, and More
Date: 2021-03-23

Customers are not product people.

Life-changing money can mean different things to different people.

A wide-funnel with a low price point allows more people to use it and it to spread.

In the early-days the low-touch and no-touch funnel is a higher percentage of your revenue base.

Episode 542 | 10x in Two Years, Past $3M ARR with SquadCast
Date: 2021-03-30

Find things people hate about competitors.

Build up soft skills to be a successful CEO.

Evolve at the pace of the company.

Pricing is very hard to get right and easy to screw up.

Pricing is the number one lever in SaaS.

Pricing can make a business that won’t work into a highly profitable one.

Don’t ask venture capitalists for capital, ask them for advice.

Brand is what people say about you when you are not in the room.

Episode 543 | All Things Startup with #Mike Taber
Date: 2021-04-01

Spiderman vs. Elsa

Episode 544 | Annual Raises, Finding Good Startup People, and More Listener Questions with Josh Pigford
Date: 2021-04-06

You can get people lower than market rate if you have advantages (team size, remote, etc.).

Nobody is going to work for your company for years at below market rates.

You should be testing and changing prices all of the time to find the optimal price point.

The biggest lever in SaaS is pricing.

You can have a whitelabel plan where they pay A LOT more to remove the branding.

Test how many click throughs you get and how many trial signups you get.

When it comes to finding good people it comes to finding people who will free you up to do other things.

People who are self-employed before joining your company (are good people to hire).

Episode 545 | The Value of Learning 80/20 Design Fundamentals
Date: 2021-04-13

The lure of self-publishing is that you get to keep 100% of your profits but it takes a lot more work.

Relying on others slows things down (in the early days).

Think critically about other designs (to learn what makes good design).

The number one thing you can do for your design is reduce clutter. (Clutter in elements, number of fonts, number of colors, grid, etc.)

Start with sketching out a framework on paper.

Your first instinct is often incorrect.

Episode 546 | Hiring Entrepreneurial People, Anonymity, Disruptive Innovation, and More Listener Questions
Date: 2021-04-20

Most bootstrapped startups are LLCs.

Until someone has 10% equity they don’t really feel like an owner.

As a bootstrapper you move extremely fast and are extremely capital efficient.

There are three types of risk when launching a new product: product risk, market risk, and execution risk.

Episode 547 | Private Podcasting, Apple’s Announcement, and Accelerating Growth with Craig Hewitt
Date: 2021-04-27

Podcast hosting becomes more of a commodity as more people get into it.

Shift from being a liability on your customer’s mental balance sheet to being an asset.

Ads are not the only way to make money with your podcast.

Episode 548 | The Grind of Building a SaaS During Nights & Weekends
Date: 2021-05-04

Don’t build too much too soon.

Being bootstrapped, speed of development is critical.

Part of being an entrepreneur is that you have a plan B and a plan C, D, and E.

There is a difference between what customers say they want and what they actually need.

Don’t take your customers literally.

Episode 549 | Hiring vs. Outsourcing, E-commerce SaaS, and More Listener Questions with Jordan Gal
Date: 2021-05-11

If you don’t have a product yet you need to figure out what this prospect wants out of it. If someone is caught up in the risk of being an early adopter then they probably aren’t a good fit for you yet.

In most cases people don’t actually know what they are doing.

Money (that you raise) can accelerate you going the wrong direction as well.

Raising money is a choice.

B2B marketing is in a pretty weird spot right now.

The funnel is no longer clearly defined.

There are no rules anymore.

Episode 550 | Three Years of Grind to Six Figures in ARR with CloudForecast
Date: 2021-05-18

The developer coding is his basement is probably not going to be your best customer.

There is a lot of value going through the (accelerator) application process once in a while.

There is value in feedback. How you take it and move forward with it is what is important.

Don’t take things at face value.

Product market fit is a journey. It is an iterative process.

There is a level of humility you need to have as founders and realizing that you don’t know everything.

Episode 551 | Task-level vs. Project-level Thinkers, No Such Thing as an Autopilot Business, and More (A Rob Solo Adventure)
Date: 2021-05-25

When people raise a bunch of money they hire project-level thinkers.

Task-level, project-level, and owner-level thinkers (are the categories).

Ownership is ownership of the results.

There is no such thing as an auto-pilot business (that goes on forever).

All auto-pilot businesses have a life spawn.

Use every advantage you have.

Ask yourself the question, “What are you really, really good at?”

Episode 552 | Google Audits, Partnerships, and Freemium with Mike Taber
Date: 2021-06-01

Added users and visibility only go so far if they don’t pay the bills iIn reference to doing an App Sumo deal).

There is competitor pain and customer pain.

Episode 553 | Stack Overflow and Moz Acquired, Quitting Instead of Giving Up Remote Work, and More Bootstrapper News
Date: 2021-06-08

For certain business outcomes you need buckets of money.

There was an idea that productivity was tied to butts in seats (pre Covid).

Companies need to have better ways of tracking quality of work.

Episode 554 | Thinking Through Your Exit + Grief and Entrepreneurship with Dr. Sherry Walling
Date: 2021-06-15

Most people aren’t good at naturally dealing with grief.

Symbols are really important.

Burnout makes our brains less flexible and fluid.

Burnout is not binary…it exists on a continuum.

A brain that is exposed to a different variety of stimulus is healthier.

Make your life work the way you want it to.

Episode 555 | Businesses You Can Bootstrap, W2 vs. Contract, Enterprise Pricing, and More Listener Questions with Ruben Gamez
Date: 2021-06-22

Be efficient with the people you have on the team.

(You can) spend money if it leads to growth.

Folks that are ambitious about growth tend to be moving towards an exit.

In general you can bootstrap almost any software company.

Look at how products are priced in your category. Look at how your competitors are pricing deals. If you aren’t getting large deals then someone else is.

Episode 556 | Zero to $26k MRR as the Solo Founder of Rails Autoscale
Date: 2021-06-29

Have a hypothesis and try to prove it or disprove it before writing a bunch of code.

It is okay to take it slow.

Freemium is a perpetual plan that is limited.

Episode 557 | Investing for Founders
Date: 2021-07-06

Get an emergency fund of three to six months in cash. Somewhere it won’t go down if the market crashes. Typically a savings account.

Inflation destroys cash. (Don’t have too much in cash either.)

Max out your retirement plans.

A 401(k) with matching is like free money.

Whole life is something to be avoided.

Index funds are the way to go.

Lazy portfolio.

Episode 558 | Thinking Through Funding as a Bootstrapper
Date: 2021-07-14

Funding is just another tool in the toolbelt.

Funding allows a founder to take more risk and potentially grow their business faster.

WIth true bootstrapping there is a ton of risk on you personally.

If you don’t have close to product market fit then you should keep grinding (rather than raise funds).

One reason that (investing in startups) works is that SaaS sales at crazy multiples.

Episode 559 | Bootstrapping a Two-Sided Marketplace with MicroAquire
Date: 2021-07-20

The main benefit of working with a broker (when selling your business) is that you don’t have to handle everything.

(Selling a business) is an emotional process.

The exit is such an important part of the founder’s journey.

There never has been a marketplace for M&A.

Working in the business is a blessing and a curse.

Episode 560 | When to Hire, Square Business Banking, and More Bootstrapper News
Date: 2021-07-27

You make a lot of it up as you are going.

Bootstrapped founders often end up hiring too late.

Timebox things.

A business is when you are starting to hire and a company is when you are starting to scale.

Building out an organization is a different skill set than building a business.

Be mindful of the joys.

Find things you should be taking joy in that you are not finding joy in.

Episode 561 | Launching on Product Hunt and DIY vs. DFY
Date: 2021-08-03

There can be a lot of inertia (with large companies). It can require lots of people’s buy in (to get your product approved).

For a ProductHunt launch, people vote early before the leaderboard has been established for the day.

The leaderboard sorts out after a few hours into the day.

Get feedback from people who have done the experiments before.

Episode 562 | “Measure Twice, Cut Once” + SaaS Holy Grails (A Rob Solo Adventure)
Date: 2021-08-10

Anytime someone says they want to edit your terms of service then your price skyrockets into the enterprise (pricing).

Charge for changes and require a minimum (annual) commitment.

Remember that the most likely outcome is that no deal happens (when you are approached for an acquisition).

Always sign an NDA before discussing financials.

Episode 563 | The Struggle, Calls to Action, Selling Above $1M ARR, and More Listener Questions
Date: 2021-08-17

The best lawyers come through referrals.

Standard way to handle (a founder leaving) is through vesting.

Get a job at companies doing interesting things (if you want to eventually start your own company).

We live in an incredible age.

Remote work is more viable than ever.

It is hard work, luck, and skill to create your next break.

It is tough to be a virtual assistant on Upwork or anywhere (if you are just starting out).

Episode 564 | Running a Business with 10,000 Paid Subscribers
Date: 2021-08-24

Figure out what people want and go from there.

Trust is heavily related to brand.

There is a level of experience and empathy in looking at nuances.

A trust bank takes a long time to build up but can drop quickly.

“Jobs to be Done” framework.

Talk to the customer.

You get addicted to the free traffic that Google is shoving down your throat.

As an entrepreneur you need to keep a level of Zen stoicism.

Episode 565 | Correlation vs. Causation, Focus, Sharing MRR, and More Listener Questions
Date: 2021-08-31

What makes people successful is that they work their ass off and build up their skills over time.

It comes down to hard work, luck, and skill.

If you want to build something big, you need to focus.

You can’t have autopilot businesses that are autopilot forever.

MRR is the key metric. Everything flows from MRR.

Growth costs money.

Fast-growing businesses are rarely profitable.

Sometimes (when you are questioning things) you need a quick win.

Doing things in public creates opportunity.

The worst result when shipping something is not that someone isn’t going to like it but that no one cares. That is actually the most likely result.

Episode 566 | From Bootstrapped to Venture Backed with Hana Mohan
Date: 2021-09-07

Hiring is a lot more competitive.

Your investors aren’t running your company for you.

Most of us bootstrap because we are outsiders. We don’t have friends and family with money.

Episode 567 | From Developer to CTO to Buying the Company for $1
Date: 2021-09-14

If there is one thing about startups it is that things change very quickly.

In a startup it is hard to see the forest for the trees.

Investors want people doing the work to have the majority of the equity.

In an investment round you usually sell between ten and twenty percent of the company.

Episode 568 | MailChimp Sells for $12 billion
Date: 2021-09-21

Going public is not an exit. It is a liquidity event.

SaaS at scale can be 30-50% net profit margin.

In startups not everything is equal or fair.

If you start a company, never tell people you aren’t going to sell or go public.

Episode 569 | The Life Changing Decision of When to Sell Your Company
Date: 2021-09-28

Today you can start (building a site) with a no-code (platform).

Building a two-sided marketplace is different.

Consumers are really price-sensitive.

Bootstrapping is more inclusive (than Silicon Valley).

Episode 570 | Bootstrappable Businesses, Selling as an Introvert, and More Listener Questions
Date: 2021-10-05

A lot of people want to start a two-sided marketplace and that is really complicated and really expensive. It is really, really rare when you have that come out of a bootstrapped company.

Don’t try to build both sides of the marketplace at once.

It is very hard to build a SaaS company if one of the founders is not a developer.

Building trust with potential customers is commonly done with content.

There are ways you can be an introvert and still make sales.

With sales you are like a high-priced consultant trying to help the person on the other end of the line.

Episode 571 | Deciding When to Move on to Your Next Idea
Date: 2021-10-12

We have patterns, predictions, and gut-feels but it is experimental.

One of the hardest things to do is to get a group of people to change their behavior.

There are a lot of form builders.

It takes a long time to write landing page copy.

Podcast: Out of Beta

Episode 572 | Fault vs. Responsibility & Games vs. Practice (A Rob Solo Adventure)
Date: 2021-10-19

It is not your fault but it is your responsibility.

As founders we have to make the decision on what to do next.

It is a mental shift to “the buck stops with you.”

Most people don’t see (the work building up to the success).

Adwords works for certain companies in certain spaces with certain budgets.

Content marketing is crowded but is not too crowded.

You have to put in reps.

Try things that are hard. Try things that are likely to fail.

Be aware of your energy levels and moods based on what you are eating and how you are sleeping.

Episode 573 | Hiring FT vs. PT, WordPress Consolidation, and More Bootstrapper News
Date: 2021-10-26

Part-time contractors are good for set, defined tasks.

Long-term planning is difficult on a part-time basis.

You need middle-managers by the time you are a 15-person company.

Episode 574 | The Deep Need to Be a Software Entrepreneur
Date: 2021-11-02

Affiliate revenue for personal finance companies is high.

Personal Capital pays $100 (for a referral).

So much of online and offline business is based on a commission.

Writing code and building a product are two different things.

You have to push through the brick wall.

Episode 575 | Shipping Code, Pivoting, and More Listener Questions with Derrick Reimer
Date: 2021-11-09

Often why people raise funding is to hire people for (specialized) roles.

Lean on building a codebase that, if the MVP proves to be viable, you can continue on that codebase and don’t have to stop and rewrite.

There is sometimes a tendency to over-test. Focus more on integration tests.

Don’t try to over-process.

Set up continuous integration early to reinforce your best practices.

Push code on branches from day one. It is a good muscle to build up.

Don’t build bad habits.

Pretend like you have a small team with you so that you are ready for when you hire one.

No one goes back and looks at design docs. They are going to look at code.

If you design something that is counterintuitive then document that somewhere.

Figure out what your key differentiator is going to be and then honing in on that really strong.

What is a burning pain point that a small subset of the market has?

The burden of (building native apps along with a web app) is very high.

Whitelabeling an app (and marketing it) can be a good stair step.

Whitelabeling has platform risk.

Episode 576 | Don’t Become a Media Company (A Rob Solo Adventure)
Date: 2021-11-16

You don’t have to ask someone permission to become an entrepreneur.

We live in the best time in history to be a creative, to be a maker, to be an entrepreneur.

The practice of gratitude is not just a better way to live day-to-day, it is a better way to stay mentally healthy and to put positivity into the world.

Building a media brand is very expensive and is a very long-term play.

Leverage every advantage you have.

Episode 577 | Finding the Right Problem to Solve
Date: 2021-11-23

Book: Jobs to be Done Playbook

Jobs to be Done gives you a language and techniques to help you point your business in the right direction–to the problems you should solve that are going to have the biggest impact in the market.

Don’t look at the people you are trying to serve through the lens of your product.

A synonym for “Jobs to be Done” is “Problems to be Solved”.

Who do you want to innovate for and where do you want to innovate (what is the problem area you want to solve for)? (The who and the what)

List all of the actors and stakeholders involved and ask, “who is going to be the ultimate consumer of the value I create?”

Episode 578 | How Mike’s Merger Panned Out
Date: 2021-11-30

(When things aren’t going well) how can you make everything into a speedbump rather than a roadblock?

In the startup world a week is a month and a month is a quarter.

To deliberate on decisions for a month or two is too long and you start losing ground.

Everyone has their own internal motivations.

What is it that gets you out of bed in the morning? What is it that excites you?

Episode 579 | The SaaS Fundraising Landscape (+The TinySeed Syndicate)
Date: 2021-12-01

There are basically two different kinds of funding options. The first is traditional primary investments–what a typical VC investment is. New money going into the company for growth. New stock is issued. North of $1MM ARR there are secondary investments available which allows a founder to de-risk and take a bit of stake off of the table.

Secondary offerings are more common now.

There are two sides to a syndicate. Investors and founders.

Episode 580 | Seven SEO Tips Every SaaS Can Use (with Ross Hudgens)
Date: 2021-12-07

Put your blog in a subfolder rather than a subdomain.

When creating keyword-focused content make the url exactly match that keyword. Everything you put in (the URL) after the keyword can dilute it.

Almost every feature page that you have on your SaaS marketing site should aim to target keyword ‘software’. (e.g. Instead of “keyword analytics” use “keyword analytics software”. This gives you that long-tail keyword.)

Don’t try to rank directly for “Best X Software”. To indirectly rank you need to reach out to each of the sites that come up on those terms and get reviews on those sites.

Use on-page content marketing best practices. (Have large fonts: 16px plus. Black font on white background rather than gray on white. Don’t have too wide column width. Get all images under 200kb–use the lowest filesize the retains image quality. Make it scannable.) This is user experience that backs into rankings.

Build passive link assets around keyword sets such as ” statistics” and ” trends”. What are things that people naturally Google to link to from their own websites.

Answer keyword questions immediately (right after the H1). You want to have the lowest time-to-value for your content.

Alternative topics are huge for SaaS SEO. (e.g. a versus article). These are low volume but high-converting.

Episode 581 | Inflation for Founders
Date: 2021-12-14

Trying to time the market is a fool’s errand.

If you find your costs are going up dramatically–most SaaS providers have pricing flexibility. You can probably raise your rates 5% to 10% over the next year.

Usually when inflation goes up commodities go up in price.

Cash is king and queen. Cash allows you to move fast and get things done.

Bonds don’t do well in inflationary times.

There are three skills: Making money. Keeping money. Growing money.

Episode 582 | Enterprise Sales, Crowdfunding, Replacing Yourself, and More Listener Questions
Date: 2021-12-21

Any kind of custom contract then it should be an enterprise plan.

HIPAA should be an enterprise plan.

Keeping code in escrow should be an enterprise plan.

Custom development work should be an enterprise plan. Make sure you retain the IP.

Integration with Salesforce should be an enterprise plan.

Integration with data warehouse software (Snowflake or Redshift) then it should be an enterprise plan.

An enterprise plan should be at least $20k or $25k a year.

Don’t confuse a sales demo with a training session.

A demo should have the product populated with data.

Listen more than you talk (when you do a demo).

If you are going to do a deck then don’t put in financial projections as the only thing you will do is disappoint your most optimistic investors.

Know your numbers. Revenue churn. ACV. For different cohorts.

Think in years–not months.

The biggest problem for most companies (not all) is finding good people.

Building a team is crucial.

Have a strong preference for action when it comes to iterating through growth channels.

Episode 583 | Finding Startup Ideas with Sam Parr
Date: 2021-12-28

SaaS is more valuable (than a media company) for a reason.

If you are a journalist, the word “content marketing” is the worst word on earth.

You start seeing patterns.

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