The Top 10 Pieces of Advice I’d Give to My Younger CEO Self

Recently a post on Twitter had my reflecting on the top advice I’d give to my younger CEO self: I missed one of the key Top 10 points — I ran out of 240 characters on Twitter), but thought it might be worth breaking them down in more detail on SaaStr below:
  1. Go Long.
This can be hard.  The first start-up I ever joined as an employee was quickly acquired for $200m, which became $1 billion (!) by the time the deal closed, we IPO’d … and then our acquirer went bankrupt.  Poof.  I lost $12,000,000 on paper in 12 months, and it went to $0.  Boy that was hard.  To lose it all. It was tough to recover from that.  And even harder to think about Going Long.  Instead, it sort of makes you think about taking the First Good
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The Top 10 Pieces of Advice I’d Give to My Younger CEO Self

Recently a post on Twitter had my reflecting on the top advice I’d give to my younger CEO self: I missed one of the key Top 10 points — I ran out of 240 characters on Twitter), but thought it might be worth breaking them down in more detail on SaaStr below:
  1. Go Long.
This can be hard.  The first start-up I ever joined as an employee was quickly acquired for $200m, which became $1 billion (!) by the time the deal closed, we IPO’d … and then our acquirer went bankrupt.  Poof.  I lost $12,000,000 on paper in 12 months, and it went to $0.  Boy that was hard.  To lose it all. It was tough to recover from that.  And even harder to think about Going Long.  Instead, it sort of makes you think about taking the First Good
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7 Thoughts on Building Your First Partner Program

Salesforce announced this past quarter that its partners were the #1 source of its new bookings. Wow.

What that exactly means, and how it’s defined is unclear, but the point stands.

Partners are a key part of getting to $100m for most of us, maybe even almost all of us.  But they rarely get us to the first $1m … usually you are too small or nascent for anyone to really want to partner with you.  I’ve seen some companies like Talkdesk get to their first $1m leveraging partnerships, but even there it still takes time.  In any event, partnerships almost always work.  But our expectations of how quickly they deliver, and how they deliver, are almost always not met ?

A few things to think about:

7 Thoughts on Building Your First Partner Program

Salesforce announced this past quarter that its partners were the #1 source of its new bookings. Wow.

What that exactly means, and how it’s defined is unclear, but the point stands.

Partners are a key part of getting to $100m for most of us, maybe even almost all of us.  But they rarely get us to the first $1m … usually you are too small or nascent for anyone to really want to partner with you.  I’ve seen some companies like Talkdesk get to their first $1m leveraging partnerships, but even there it still takes time.  In any event, partnerships almost always work.  But our expectations of how quickly they deliver, and how they deliver, are almost always not met ?

A few things to think about:

Small Checks From Large Venture Funds: Maybe One is Enough

Apologies in advance to my friends and colleagues that will disagree and/or dislike this post.  But anyhow … The world of venture fundraising has changed again dramatically the past 24 months.  250+ new seed funds have been raised (wow!) in the past 24 months.  That really is crazy.  And Big Funds have added even more growth capital, bigger core funds, and in many cases, more seed capital themselves.  Competition for the hottest deals is at an all-time high in SaaS (yes, B2B trails B2D by 3-4 years, so now we are catching up there, too). Net net, this means a new explosion of types of funds you can raise capital from in the early-ish days … if you fit the narrow mold of venture fundable startups. This doesn’t mean getting funded is easier.  In fact, even with all these new funds and new Continue reading "Small Checks From Large Venture Funds: Maybe One is Enough"

Over 160 Venture Capitalists already purchased their Unicorn Hunting Licenses for 2018…

Year after year, VCs show up to SaaStr Annual locked and loaded, term sheets in hands, on the hunt for soon-to-be Unicorns to add to their portfolios. From the Founding Partners, Managing Directors and big name SaaS VCs who grace the stage — like 10X unicorn investor Jason Green of EmCap or SaaS legend Tomasz Tunguz, to the firms that send over a dozen of their Partners and Associates — everyone who invests in SaaS has a presence at SaaStr Annual. We also see some private equity firms registering early, and the list of publicly traded companies sending Corporate Development teams is at least 2Xing year over year. Whether you’re in it for the long haul and need cash to scale, or you’re looking for a speedy exit — or even if your dream is to become part of something bigger, where you can watch your product live
SaaStr Annual Silicon Valley VC Term Sheets - fundraising deals get done at SaaStr. Matt Garratt, VP, Salesforce Ventures
Mamoon Hamid, Managing Director, SaaStr Annual Strategy Stage
Tomasz Tunguz, Redpoint Ventures, at SaaStr Annual
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The Top 10 Mistakes First Time SaaS Founders Make

Just about 2 years ago, we put together a post that summarized all our learnings from working with great first-time founders.  Founders far better than me.  And as amazing as they are … they all tend to make the same set of mistakes in scaling SaaS.  It’s human nature.  But if you avoid just a few of this mistakes, boy, you can scale so much faster.  And have less stress and drama just when it’s starting to get good. I challenged myself to dust off the list and see if two years later, the list would be the same.  Some of the points have evolved.  But the list seems to still stand two years later.  So I’ve updated it and the learnings below. — Jason, ed. Second-timers know the playbook and can execute against it faster.  But often times, they also have
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After $2m in ARR — Start Specializing Your Sales Team

There’s a set of questions I get asked all the time:
  • Should you pay sales reps on renewals?
  • Should you pay sales reps on upsells a long time down the road?
  • Should you pay sales reps on … ?
I am a huge proponent of paying sales professionals well.  But for these sorts of questions, my answer is almost always: No.  Pay closers on closing.  Period.  At least, after you are past $2m or so and are ready to expand the sales team at least a tiny bit.

Why? Because you want to specialize.  You need to, to scale in SaaS.  We’ve all learned this over the past decade in SaaS:

Top Hack: Keeping a “Stub” Source of Capital in Your Back Pocket

One of the wonderful things that has changed in the years since I was running my own SaaS company is the rise of “stub” sources of capital.  Investors that, for a variety of reasons, are OK buying fewer shares than the average investor, and often, outside of the timing of traditional venture rounds. The most visceral example is how the top startups out of YCombinator Demo Day raise money.  For the top YC companies, there is always more investors than room to invest, and the startups are often fairly capital efficient.  This combo means they can leverage Demo Days to fine tune the exact amount of capital they want to raise. I wish I had had that luxury.  I didn’t have trouble raising traditional venture rounds.  But the gap in between rounds was tougher. When EchoSign was at about $6m in ARR and growing nicely, and cash flow positive,
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Top Hack: Keeping a “Stub” Source of Capital in Your Back Pocket

One of the wonderful things that has changed in the years since I was running my own SaaS company is the rise of “stub” sources of capital.  Investors that, for a variety of reasons, are OK buying fewer shares than the average investor, and often, outside of the timing of traditional venture rounds. The most visceral example is how the top startups out of YCombinator Demo Day raise money.  For the top YC companies, there is always more investors than room to invest, and the startups are often fairly capital efficient.  This combo means they can leverage Demo Days to fine tune the exact amount of capital they want to raise. I wish I had had that luxury.  I didn’t have trouble raising traditional venture rounds.  But the gap in between rounds was tougher. When EchoSign was at about $6m in ARR and growing nicely, and cash flow positive,
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