Why did Jason M. Lemkin change his point of view on the value of a COO for an early stage startup?

I try to work with (and invest in) CEOs that are better than me. I found, when I was a SaaS CEO, that the CEOs that complained about needed a COO early, that it was too hard (which it is), etc. … they all failed or came up way short. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. Or didn’t want to do sales. Or couldn’t stand your CTO. I still believe this. When I hear a CEO want to not deal with a functional area anymore that isn’t yet built out, that’s a big flag. But … I didn’t fully get how complex it all gets after $10m-$20m ARR if you really want to go big. I still believe a CEO should “do it all” in terms of building a decent management Continue reading "Why did Jason M. Lemkin change his point of view on the value of a COO for an early stage startup?"

How much time does Jason Lemkin spend answering questions on Quora?

I try to spend about 20 minutes a day. I really enjoy writing on focused questions, it sharpens the mind and more specifically, helps me collect and “succinct-ify” my thoughts on questions I’ve already been thinking about. The trick is I only answer questions I’m very personally interested in, and already can compose an answer in my head before I start typing. Then, it’s a fun break, rather than a chore. Traditional blogging has become a chore, although once I write something good, I feel pretty good after. View original question on quora The post How much time does Jason Lemkin spend answering questions on Quora? appeared first on SaaStr.

Is Salesforce good for startups?

The one thing I do strongly recommend is letting each VP you hire pick her core tools and system of record. Forcing a VP of Sales to use a CRM she hasn’t used before or isn’t comfortable with is a huge tax on her time. Don’t do it. Same with your VP of Marketing and your Marketing Automation system, etc. If you like Hubspot but your VP of Marketing likes Marketo … go with Marketo. Given Salesforce’s overwhelming market share in tech companies in particular, your VP of Sales, once you hire her or him, is likely going to want to use Salesforce. So at least plan on using Salesforce once you hire your VP of Sales. Forcing a VP of Sales to use a CRM she isn’t comfortable with is a significant drag on productivity — and thus, sales. Don’t do this. Should you use Salesforce before then? Well, Continue reading "Is Salesforce good for startups?"

What is the best piece of advice on closing deals for a new, inexperienced salesman?

Add value. Most new salespeople focus a lot on the transaction. What’s your budget? Do you need a discount? How big a discount? Can I give you a bigger discount? What questions do you have? If I give you an even bigger discount, can you sign right now? Your discount will expire if you don’t sign today! This is OK in super high velocity inside sales. Not great but OK. Discounting is, for better or worse, part of the standard sales toolkit. But the reality though is they miss the best question in SaaS sales. “What problems can I help you solve today?” Start with that. Build that relationship. Map out how your product, and others, can solve your prospect’s problems. Explain it, take the extra time. Do a demo. Show them. Thank them. Never, ever, never say a prospect is wasting your time. No. They are investing their Continue reading "What is the best piece of advice on closing deals for a new, inexperienced salesman?"

As an early employee, I own a part of a startup that’s about to IPO. These shares constitutes almost all of my wealth. As an aspiring conservative value investor of age 30, how much and at what rate should I sell off my shares after the IPO?

Goodness. Congratulations on the IPO! But what and how to sell is really a tough one. If you’d sold shares in almost any SaaS/Cloud IPO in the past 7 years, you’d feel a bit of a fool: I did. 🙁 But it’s hard to know. Marc Benioff sold a huge amount of his Salesforce stock before its run from $2b to $85b in market cap.
  • Can you afford to lose it?
  • How much are you OK risking?
Everyone is a Genius in 2018. Some general thoughts though:

How will the proliferation of micro funds led by first-time investors change the early-stage funding landscape?

There are 500+ new sub $200m funds raised since 2011, and my guess is 200+ in the past 2.5 years: VC funds at / below $200M in size (new funds raised since 2011) This is great for founders:
  • First time investors are generally less ownership sensitive. The longer you do it, the more you feel you need to own of each investment. You learn that owning just a little of most non-decacorns just doesn’t move the needle for fund economics — unfortunately. New investors are generally less sensitive to the % they own, and just want to get into as many good deals as they can.
  • Some first time investors are less valuation sensitive. Some again just want to get into good deals. Not all, but enough.
  • First time investors have more time to help. Once you’ve been doing it for a while, you are just on too many Continue reading "How will the proliferation of micro funds led by first-time investors change the early-stage funding landscape?"

What was your first entrepreneurial adventure? What was your last? Which did you enjoy the most and why?

My first entrepreneurial adventure was in the crazy days of Web 1.0:
  • I joined one of my clients as a Director of Corporate Development in 1998. This was my first start-up job. It was a great job and I was very lucky to have it. Great founders and a super cool SOMA office. My “desk” was a door laid down between two file cabinets. I lunched in South Park (the South Park before the VCs moved in). I loved everyone I worked with. I had an excuse to use the Internet all day. We were a market/segment leader. It was great.
  • The first day on the job I had to fire someone on the management team who I’d never met before. That was crazy. I’d never fired or hired anyone.
  • The second week we had an offer from Amazon to invest in the company at a $100m-$150m valuation or
    Continue reading "What was your first entrepreneurial adventure? What was your last? Which did you enjoy the most and why?"

Do venture capitalists use Docsend when sending fundraising pitches to LPs?

I didn’t when I raised my first fund. I was in Sell mode. I wanted to make it as easy as possible for the LPs to buy. I sent a PDF and a link to a Google Sheet. I wanted them to Buy. But now … I send protected documents. New LPs get protected documents. Existing LPs get documents uploaded to a portal and protected as well. I also no longer send unencrypted email updates to my LPs. I send a teaser, and they have to enter protected documents. Now, I’m not really selling. And compliance is more important. Time and the context moves on. View original question on quora The post Do venture capitalists use Docsend when sending fundraising pitches to LPs? appeared first on SaaStr.

What is the difference between running a 10 person startup and a 100 person startup?

The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for many CEOs is letting go. By employee 100, you have to let go of things. You have to let go of being the product manager. You have to let go of what you say being almost divinely correct. You have to let go of the many mistakes which will be made. You have to let go of the fact that some important things will be done “worse” than if you were doing them or managing them yourself. You have to let go, and learn to backfill the team you build. View original question on quora The post What is the difference between running a 10 Continue reading "What is the difference between running a 10 person startup and a 100 person startup?"