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DEAR SAASTR: WHAT ARE YOUR THOUGHTS ON CO-CEOS?

The role of CEO is so odd as it is, thinking through the implications of why a co-CEO situation might work is helpful and in this case, Jason Lemkin has mellowed a bit over the years on it. YMMV but it really depends on the situation at hand.

2023.11.10
saastr.com2 min readTLDR Founders

Sponsored

STYLO [6] is an AI assistant that lives inside every Zendesk ticket to solve your 10-MINUTE TICKETS IN 10 SECONDS. Stylo automatically creates answers from your Guide Help Center, translates messages, standardizes agent tone, and more. Customers get (correct) answers fast; agents do less gruntwork 🙌

2023.11.08
askstylo.comSponsorTLDR Founders

THE OPENAI KEYNOTE

Sam Altman took to the stage to announce new products and features available from OpenAI at the company’s first-ever developer conference. Here’s a long take that breaks down the talk and the key takeaways.

2023.11.08
stratechery.com19 min readTLDR Founders

MORE GOOD NEWS IN STARTUPLAND

DataDog announced earnings that beat plans. In its earnings call, it mentions that it’s seeing signs that the cost-cutting activities that dominated the start of this year are plateauing, which hopefully acts as a signal of good news for tech.

2023.11.08
tomtunguz.com2 min readTLDR Founders

CAN MOST “PRETTY GOOD” SALES REPS SELL ANY SAAS PRODUCT?

Probably not. When hiring salespeople, dig into these points. Known brands are easier to sell, and enterprise SaaS is meaningfully different from SaaS built for smaller businesses. Only the very best salespeople can context switch between SaaS effectively.

2023.11.08
saastr.com2 min readTLDR Founders

YOUR BUSINESS MODEL DRIVES YOUR MEASUREMENT

Usage-based pricing seems to be rising in popularity. It’s a revenue model that scales value for both parties as a customer uses your product more. What metric you decide to pivot your pricing around is hard to land on. This metric is commonly called the “Value Metric”. Here’s a breakdown of metrics used by some top companies.

2023.11.08
mostlymetrics.com5 min readTLDR Founders

SOFTWARE MARKET GENES

Software building on top of open-source LLMs, how defensible is that? A lot of AI, much like vertical SaaS, is a winner-take-most market. Investors and founders are racing to reach an inflection point that brings down their CAC and makes market capture increasingly easier.

2023.11.08
akashbajwa.substack.com6 min readTLDR Founders

TRANSPARENCY IS HARD TO DO WELL

Teams with high trust often function more efficiently. Trust requires a degree of transparency, but transparency can be unsettling without context. How you share information is just as important as what you share.

2023.11.08
breakingpoint.tech4 min readTLDR Founders

A JOB IS JUST A PHASE IN SOMEONE’S LIFE

Managers and employees often play this bizarre game where they pretend the employee will be working at the company forever. That’s never the case and the company won’t be around forever either. Honest conversations about career ambitions will help with retention and trust building.

2023.11.08
critter.blog2 min readTLDR Founders

Sponsored

ZENDESK

Every customer counts when you're a startup. Zendesk [5] gives you the tools and resources you need to build lasting relationships from the start. And with Zendesk for Startups [5] you’ll get everything you need — free: 🆓 6 months of Zendesk Suite and Zendesk Sales CRM [5].

2023.11.06
zendesk.comSponsorTLDR Founders

OPENAI IS A LOT MORE VULNERABLE THAN YOU THINK

On the heels of OpenAI releasing functionality that decimated half of the GPT-wrapper companies, here is a contrarian view of the blind spots and weaknesses of OpenAI as this market continues to evolve.

2023.11.06
bigtechnology.com4 min readTLDR Founders

SAAS UNICORNS EXPANDING THEIR TAM THROUGH ACQUISITIONS

Larger SaaS companies like HubSpot and Clari are making acquisitions to diversify their offerings during a period of low capital funding, increasing user expectations, and growing resentment for running operations on dozens of point solutions.

2023.11.06
davidcummings.org3 min readTLDR Founders

HOW TO PREPARE FOR AN UPTURN

We’re almost 2 years into this “recession”, and at some point, we’re going to turn a corner. All of that belt-tightening and pain is going to switch and entrepreneurs need to be ready to make the switch to growth again. This is a great read on how to hopefully read the tea leaves and ride the next wave.

2023.11.06
nfx.com5 min readTLDR Founders

UNWINDING B2B SAAS GROWTH IN THE CURRENT MARKET

As interest rates rise and funding dries, boards and leadership everywhere are expecting their GTM teams to operate more efficiently. This article unpacks what this actually involves, from bringing your data and sales teams closer together to refining your ICP and target audience.

2023.11.06
goinglongblog.com6 min readTLDR Founders

WHAT DOES A GOOD NURTURE EMAIL LOOK LIKE?

Excellent tips on how to upgrade your email nurturing once a prospective customer lands on your website, reads content, or creates an account. Make it personal and optimize for the action you want, not click-throughs.

2023.11.06
linkedin.com2 min readTLDR Founders

THE ADVANTAGE OF HAVING VENTURE-BACKED FRIENDS

Your network becomes your de facto personal board of advisors. Having people who are a few steps ahead of you in the game you’re playing, who you can ask your dumb questions to, is exceptionally helpful. Ask yourself if you have these people, and if you don’t, go and find them.

2023.11.06
thisisgoingtobebig.com3 min readTLDR Founders

MEASURE TWICE, CUT ONCE

We’ve all heard the phrase “measure twice, cut once” before. But does it hold true in the startup world, where we’re told to move fast and break things? There are certainly some big decision areas where prudence is needed: layoffs, signing multi-year big contracts, or making big investments. Plan, plan, and plan again.

2023.11.06
startupceo.com2 min readTLDR Founders

THOUGHTS ON WRITING AND PUBLISHING PRIMER

A really transparent take on publishing your own book in this day and age. Will Larson takes you through his previous books and around the decisions and financials around publishing his latest one. If you’ve ever thought about publishing a book, this is a great primer.

2023.11.06
lethain.com5 min readTLDR Founders

IS 5 FOUNDERS TOO MANY FOR THE VENTURE GAME?

Pipedive had 5 co-founders and sold for $1.5bn, so it can work. However, that’s probably the exception and not the rule. Generally, anything with over 3 co-founders starts to get complicated, from both an equity and management perspective.

2023.11.06
saastr.com1 min readTLDR Founders

HOW TO HIRE WHILE AVOIDING FUTURE LAYOFFS

We’re on the cusp of another potential upswing but we don’t want to get out over our skis. Some really simple advice on how to continue hiring while still avoiding future layoffs.

2023.11.06
news.crunchbase.com3 min readTLDR Founders

VCS NO LONGER DO DTC

If you’re a consumer goods company trying to raise right now, it’s super hard. So far this year, U.S. investors put just over $130 million into companies at the intersection of e-commerce and consumer products. That’s a whopping 97% decline from the peak in 2021.

2023.11.03
news.crunchbase.com2 min readTLDR Founders

UNPACKING AMAZON’S UNIQUE WAYS OF WORKING (93 MINUTE PODCAST)

This podcast is with Bill Carr, someone who played a pivotal role in shaping Amazon’s digital music and video strategy over the course of 15 years. There are a ton of excellent takeaways, but a highlight for me was how to actually follow the “disagree and commit” principle.

2023.11.03
lennysnewsletter.comTLDR Founders

TOP 10 MISTAKES WHEN HIRING A VP OF SALES

Cautionary tales and sage advice for founders hiring their sales leaders. It’s about understanding the career game they’re looking to play, testing their knowledge of your product, and seeing if they’re going to attract sales talent to your company.

2023.11.03
saastr.com6 min readTLDR Founders

ARE BIGGER TEAMS BETTER?

A quick read by Sean Byrnes about when to think about big vs. small teams. The short answer is that it depends, but he breaks it down in an easy-to-understand fashion.

2023.11.03
breakingpoint.tech4 min readTLDR Founders

WHAT MAKES A GREAT ACQUISITION?

Google has made over 250 acquisitions. Facebook, Amazon, and Apple have over 100 each. Getting M&A right has been the difference between reasonably successful companies, and hyper-successful ones. But M&A is really hard. This article unpacks some of the elements of great acquisitions in this long read. Most of the case studies are late-stage companies, but the principles remain true if you’re an earlier-stage company looking to acquire.

2023.11.03
thegeneralist.substack.com21 min readTLDR Founders

THE GENERATIONAL BUSINESS TRAP

This post explores the concept of "The Generational Business Trap." The discussion is around how companies, even successful ones, can fall into the trap of becoming a 'generational' business that fails to evolve with changing times and customer preferences. The key to longevity is continuously reinventing oneself, maintaining customer-centricity, and fostering an innovative culture. The post also provides examples and offers practical tips for avoiding this trap.

2023.11.03
anu.substack.com8 min readTLDR Founders

WHAT MAKES A GREAT ACQUISITION?

This is a pretty in-depth look at acquisitions from a couple of different perspectives and covers the good, bad, and ugly around how to make them stick and be successful.

2023.11.03
thegeneralist.substack.com7 min readTLDR Founders

HOW MUCH SHOULD QUOTAS INCREASE NEXT YEAR?

Even with the uncertainty in the market these days, expectations show that software purchasing will increase by as much as 8% next year. What kind of impact will that have on quotas especially given the pain CFO’s have exerted over the last year?

2023.11.03
tomtunguz.com2 min readTLDR Founders