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@DaveMcClure 
@500Startups http://500.co 
Angel Summit, Dallas, Nov 2014 
“The Lean Investor” 
Make Lots of Little Bets. 
Expect Most to Fail.
Dave McClure 
Founding Partner & Chief Troublemaker, 500 Startups 
00’s & 10’s: 
• VC: Founders Fund, Facebook fbFund, 500 Startups 
• Angel: Mashery, Mint.com, SlideShare, Twilio, Wildfire, SendGrid 
• Marketing: PayPal, Simply Hired, Mint.com, O’Reilly 
! 
! 
80’s & 90’s: 
• Entrepreneur: Aslan Computing (acq’d by Servinet/Panurgy) 
• Developer: Windows / SQL DB consultant (Intel, MSFT) 
• Engineer: Johns Hopkins‘88, BS Eng / Applied Math
Global Seed Fund & Startup Accelerator 
• What is 500? 
500 Startups 
– $125M silicon valley VC fund + startup accelerator 
– 40 people / 15 investing partners 
– Locations: SV/SF, MEX, BRZ, IND, CHN/TWN, KOR, SE Asia, MENA 
– 2000+ Founders / 200+ Mentors 
– Community + Content + Conferences 
! 
• 900+ Portfolio Co’s / 40+ Countries 
– Wildfire (acq GOOG, $350M) 
– MakerBot (acq SSYS, $400M) 
– Viki (acq Rakuten, $200M) 
– Simple (acq BBVA, $117M) 
– Credit Karma 
– Twilio 
– SendGrid 
– Udemy 
– TheRealReal 
– Barkbox 
– HomeJoy
Portfolio Diversification 
“Spray, not Pray”
500 Strategy: Lots of Little Bets* 
1) make lots of little 
bets on pre-traction, 
early-stage startups 
3) wait 3-10 years for returns: 
-10-20% small exits @1-5X ($5-25M+) 
-5-10% larger exits @10-20X ($25-250M+) 
-0-1% unicorns @25-50X ($500M-1B+) 
*See Peter Sims book: “Little Bets” 
2) over the next 2 years, 
double-down on top 20%
Why Invest in Startups? 
Bad Reasons: 
• You want to run your own 
business but don’t have the time 
• You think you can make a lot of 
money 
• You like telling other people 
what to do 
• You think it will be easy 
• You like bragging about your 
investments to other people 
Good Reasons: 
• It’s fun & you like tech stuff :) 
• You like the domain area & 
have relevant skills 
• You can afford to lose 
everything you invest 
• You’ve got time to help mentor 
and monitor your investments 
• You’ve built your own business 
before, and had both success 
and failure
Investment Thesis 
+ Your Brand 
• Invest in things & people you know & like 
• What’s your superpower? Got money, advice, skills? 
• Choose an industry vertical, customer segment, or 
skillset / domain where you can add value 
! 
• Write about your thesis / ideas / companies 
• Get on Angel List, see what’s happening in that area 
• Co-invest with other smart/famous people 
• Make a few small investments to get the hang of things 
• Say no quickly. Write checks quickly. Don’t be an ass.
The Lean Investor 
Make lots of little bets: 
• Start with many small “experiments” 
• Filter out failures + small wins 
• Double-down on stuff that looks like it’s working 
! 
• Incubation: $0-100K (“Build & Validate Product”) 
• Seed: $100K-$1M (“Test & Grow Marketing Channels””) 
• Venture: $1M-$10M (“Maximize Growth & Revenue”)
Startup Risk Reduction 
Concept 
Early 
Customer 
Usage 
Scalable 
Customer 
Acquisition 
Profitable 
Unit 
Economics 
Functional 
Prototype 
Scalable 
Profitable 
Business 
PRODUCT 
MARKET 
REVENUE 
Exit?
Investment Stage #1: 
Product Validation + Customer Usage 
• Structure 
– 1-3 founders 
– $25-$100K investment 
– Incubator environment: multiple peers, mentors/advisors 
! 
• Test Functional Prototype / “Minimum Viable Product” (MVP): 
– Prototype->Alpha, ~3-6 months 
– Develop Minimal Critical Feature Set => Get to “It Works! Someone Uses It.” 
– Improve Design & Usability, Setup Conversion Metrics 
– Test Small-Scale Customer Adoption (10-1000 users) 
! 
• Demonstrate Concept, Reduce Product Risk, Test Functional Use 
• Develop Metrics & Filter for Possible Future Investment
Investment Stage #2: 
Market Validation + Revenue Testing 
• Structure 
– 2-10 person team 
– $100K-$1M investment 
– Syndicate of Angel Investors / Small VC Funds 
! 
• Improve Product, Expand Customers, Test Revenue: 
– Alpha->Beta, ~6-12 months 
– Scale Customer Adoption => “Many People Use It, & They Pay.” 
– Test Marketing Campaigns, Customer Acquisition Channels + Cost 
– Test Revenue Generation, Find Profitable Customer Segments 
! 
• Prove Solution/Benefit, Assess Market Size 
• Test Channel Cost, Revenue Opportunity 
• Determine Org Structure, Key Hires
Investment Stage #3: 
Revenue Validation + Growth 
• Structure 
– 5-25 person team 
– $1M-$10M investment 
– Seed & Venture Investors 
! 
• Make Money (or Go Big), Get to Sustainability: 
– Beta->Production, 12-24 months 
– Revenue / Growth => “We Can Make (a lot of) Money!” 
– Mktg Plan => Predictable Channels / Campaigns + Budget 
– Scalability & Infrastructure, Customer Service & Operations 
– Connect with Distribution Partners, Expand Growth 
! 
• Prove/Expand Market, Operationalize Business 
• Future Milestones: Profitable/Sustainable, Exit Options
Startup Due Diligence 
pro tip: focus on product + customers over team + market 
• Business Plans 
• Revenue Projections 
! 
• Can The Team Build the Product? Can They Ship, Market, & Sell? 
• Are They Liars, Crooks, or Fools? Are They Lazy or Slow? Are They Crazy? 
! 
• Does Product Work? Does It Solve a Problem? Better Than Competition? 
• Are There Users / Customers? How Many? Do They Pay? How Much? 
• Are the Unit Economics Profitable? What is timing of Revenue / Expense? 
• Does The Customer Acquisition Strategy Scale? Show Me The Proof. 
! 
• Will The Business Survive & Grow? Will the Founders Quit? Sell Early? 
• If It Works, Will Anybody Buy The Business? Who / Why / How?
Docs & Legal: KISS 
• In your first 5-10 deals, co-invest w/ other smart, 
experienced investors & let them handle docs 
• *pro tip: work w/ lawyers who have 50+ Silicon Valley deals 
• Don’t get bogged down in legal BS; get the deal done 
! 
• confirm your understanding of the deal (valuation/cap, 
amount, terms) in email or text and ask for reply 
• convertible notes / security — use a cap 
• Ask for information rights 
• Ask for pro-rata rights (or min follow-on) 
• use our free KISS docs: 500.co/kiss
Investor Ecosystem 
!! 
Angels & 
Incubators 
($0-10M) 
! 
“Micro-VC” Funds 
($10-100M) 
“Big” VC Funds 
($100-500M) 
“Mega” VC Funds 
(>$500M) 
Incubation 
0-$100K 
Seed 
$100K-$1M 
Series A/B 
$2-10M 
Series B/C 
$10-50M 
Bootstrap, KickStarter, 
AngelList, Crowdfunding
Building a Portfolio Budget & 
Allocation Strategy 
• How long will it take companies to exit? (3-7 yrs) 
• How much money do you have to lose? (<5-10% net worth) 
• (How much time do you have to spend/waste? sure about that?) 
! 
• Simple allocation for $1M investment budget over 5 years 
• 50% 1st checks + 50% 2nd checks 
• 20 x 1st checks @ $25K each, 1 / qtr ($500K) 
• 5 x 2nd checks @ $100K each, 1 / year ($500K) 
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 
1 2 3 4 5
Tracking Your Investments 
• Set expectations for monthly investor updates & hold accountable 
• Get & review monthly/quarterly financials 
• WATCH THE BURN: ask what the monthly [net] burn rate is & 
compare to previous 
• WATCH THE CASH: ask how much cash is left & calc # months @ 
current burn rate 
! 
• Raise new round before <6-9 mo’s cash; Worry if <3 mo’s of cash. 
• Share info with co-investors about how your companies are doing 
(they may have diff info) 
• Focus your energy on things that are working. 
• Remember: try to be helpful, do no harm, don’t be an ass.
When / How to Double-Down? 
• When to “follow-on” (write 2nd check): 
• user/customers are scaling 
• revenue/profit is increasing 
• unit economics improving 
• other experienced investors putting in more money 
• founders never talk about selling / don’t ask for your money 
! 
• When NOT to double-down: 
• founders begging you for money 
• still no product / no revenue / un-profitable 
• team isn’t shipping product fast / frequent 
• valuation too high / raised too much money 
• can’t increase ownership by at least 50-100% 
• even if making progress; exit still not likely 
• you have other / better alternatives
The Flat, The Elbow, The Wall 
• Invest @ “The Flat” 
when prices are low 
Good Shit 
• Double-down if/when 
Happening Startup W 
you detect “The Elbow” 
(if valuation isn’t crazy) 
! 
• Don’t invest @ “The 
Wall” unless capital is 
“The Elbow” 
infinite — if valuation 
starts running away, you 
usually can’t buy any 
meaningful ownership 
relative to existing. Time 
Startup L 
Startup K 
“The Flat” 
“The Wall” 
3 
2 
1 
3
Questions? Comments? 
• More? 
– http://500.co (our company) 
– http://500hats.com (my blog) 
– https://angel.co/500startups (our fund) 
– Dave McClure, @DaveMcClure

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The Lean Investor (Dallas, Nov 2014)

  • 1. @DaveMcClure @500Startups http://500.co Angel Summit, Dallas, Nov 2014 “The Lean Investor” Make Lots of Little Bets. Expect Most to Fail.
  • 2. Dave McClure Founding Partner & Chief Troublemaker, 500 Startups 00’s & 10’s: • VC: Founders Fund, Facebook fbFund, 500 Startups • Angel: Mashery, Mint.com, SlideShare, Twilio, Wildfire, SendGrid • Marketing: PayPal, Simply Hired, Mint.com, O’Reilly ! ! 80’s & 90’s: • Entrepreneur: Aslan Computing (acq’d by Servinet/Panurgy) • Developer: Windows / SQL DB consultant (Intel, MSFT) • Engineer: Johns Hopkins‘88, BS Eng / Applied Math
  • 3. Global Seed Fund & Startup Accelerator • What is 500? 500 Startups – $125M silicon valley VC fund + startup accelerator – 40 people / 15 investing partners – Locations: SV/SF, MEX, BRZ, IND, CHN/TWN, KOR, SE Asia, MENA – 2000+ Founders / 200+ Mentors – Community + Content + Conferences ! • 900+ Portfolio Co’s / 40+ Countries – Wildfire (acq GOOG, $350M) – MakerBot (acq SSYS, $400M) – Viki (acq Rakuten, $200M) – Simple (acq BBVA, $117M) – Credit Karma – Twilio – SendGrid – Udemy – TheRealReal – Barkbox – HomeJoy
  • 5. 500 Strategy: Lots of Little Bets* 1) make lots of little bets on pre-traction, early-stage startups 3) wait 3-10 years for returns: -10-20% small exits @1-5X ($5-25M+) -5-10% larger exits @10-20X ($25-250M+) -0-1% unicorns @25-50X ($500M-1B+) *See Peter Sims book: “Little Bets” 2) over the next 2 years, double-down on top 20%
  • 6. Why Invest in Startups? Bad Reasons: • You want to run your own business but don’t have the time • You think you can make a lot of money • You like telling other people what to do • You think it will be easy • You like bragging about your investments to other people Good Reasons: • It’s fun & you like tech stuff :) • You like the domain area & have relevant skills • You can afford to lose everything you invest • You’ve got time to help mentor and monitor your investments • You’ve built your own business before, and had both success and failure
  • 7. Investment Thesis + Your Brand • Invest in things & people you know & like • What’s your superpower? Got money, advice, skills? • Choose an industry vertical, customer segment, or skillset / domain where you can add value ! • Write about your thesis / ideas / companies • Get on Angel List, see what’s happening in that area • Co-invest with other smart/famous people • Make a few small investments to get the hang of things • Say no quickly. Write checks quickly. Don’t be an ass.
  • 8. The Lean Investor Make lots of little bets: • Start with many small “experiments” • Filter out failures + small wins • Double-down on stuff that looks like it’s working ! • Incubation: $0-100K (“Build & Validate Product”) • Seed: $100K-$1M (“Test & Grow Marketing Channels””) • Venture: $1M-$10M (“Maximize Growth & Revenue”)
  • 9. Startup Risk Reduction Concept Early Customer Usage Scalable Customer Acquisition Profitable Unit Economics Functional Prototype Scalable Profitable Business PRODUCT MARKET REVENUE Exit?
  • 10. Investment Stage #1: Product Validation + Customer Usage • Structure – 1-3 founders – $25-$100K investment – Incubator environment: multiple peers, mentors/advisors ! • Test Functional Prototype / “Minimum Viable Product” (MVP): – Prototype->Alpha, ~3-6 months – Develop Minimal Critical Feature Set => Get to “It Works! Someone Uses It.” – Improve Design & Usability, Setup Conversion Metrics – Test Small-Scale Customer Adoption (10-1000 users) ! • Demonstrate Concept, Reduce Product Risk, Test Functional Use • Develop Metrics & Filter for Possible Future Investment
  • 11. Investment Stage #2: Market Validation + Revenue Testing • Structure – 2-10 person team – $100K-$1M investment – Syndicate of Angel Investors / Small VC Funds ! • Improve Product, Expand Customers, Test Revenue: – Alpha->Beta, ~6-12 months – Scale Customer Adoption => “Many People Use It, & They Pay.” – Test Marketing Campaigns, Customer Acquisition Channels + Cost – Test Revenue Generation, Find Profitable Customer Segments ! • Prove Solution/Benefit, Assess Market Size • Test Channel Cost, Revenue Opportunity • Determine Org Structure, Key Hires
  • 12. Investment Stage #3: Revenue Validation + Growth • Structure – 5-25 person team – $1M-$10M investment – Seed & Venture Investors ! • Make Money (or Go Big), Get to Sustainability: – Beta->Production, 12-24 months – Revenue / Growth => “We Can Make (a lot of) Money!” – Mktg Plan => Predictable Channels / Campaigns + Budget – Scalability & Infrastructure, Customer Service & Operations – Connect with Distribution Partners, Expand Growth ! • Prove/Expand Market, Operationalize Business • Future Milestones: Profitable/Sustainable, Exit Options
  • 13. Startup Due Diligence pro tip: focus on product + customers over team + market • Business Plans • Revenue Projections ! • Can The Team Build the Product? Can They Ship, Market, & Sell? • Are They Liars, Crooks, or Fools? Are They Lazy or Slow? Are They Crazy? ! • Does Product Work? Does It Solve a Problem? Better Than Competition? • Are There Users / Customers? How Many? Do They Pay? How Much? • Are the Unit Economics Profitable? What is timing of Revenue / Expense? • Does The Customer Acquisition Strategy Scale? Show Me The Proof. ! • Will The Business Survive & Grow? Will the Founders Quit? Sell Early? • If It Works, Will Anybody Buy The Business? Who / Why / How?
  • 14. Docs & Legal: KISS • In your first 5-10 deals, co-invest w/ other smart, experienced investors & let them handle docs • *pro tip: work w/ lawyers who have 50+ Silicon Valley deals • Don’t get bogged down in legal BS; get the deal done ! • confirm your understanding of the deal (valuation/cap, amount, terms) in email or text and ask for reply • convertible notes / security — use a cap • Ask for information rights • Ask for pro-rata rights (or min follow-on) • use our free KISS docs: 500.co/kiss
  • 15. Investor Ecosystem !! Angels & Incubators ($0-10M) ! “Micro-VC” Funds ($10-100M) “Big” VC Funds ($100-500M) “Mega” VC Funds (>$500M) Incubation 0-$100K Seed $100K-$1M Series A/B $2-10M Series B/C $10-50M Bootstrap, KickStarter, AngelList, Crowdfunding
  • 16. Building a Portfolio Budget & Allocation Strategy • How long will it take companies to exit? (3-7 yrs) • How much money do you have to lose? (<5-10% net worth) • (How much time do you have to spend/waste? sure about that?) ! • Simple allocation for $1M investment budget over 5 years • 50% 1st checks + 50% 2nd checks • 20 x 1st checks @ $25K each, 1 / qtr ($500K) • 5 x 2nd checks @ $100K each, 1 / year ($500K) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 1 2 3 4 5
  • 17. Tracking Your Investments • Set expectations for monthly investor updates & hold accountable • Get & review monthly/quarterly financials • WATCH THE BURN: ask what the monthly [net] burn rate is & compare to previous • WATCH THE CASH: ask how much cash is left & calc # months @ current burn rate ! • Raise new round before <6-9 mo’s cash; Worry if <3 mo’s of cash. • Share info with co-investors about how your companies are doing (they may have diff info) • Focus your energy on things that are working. • Remember: try to be helpful, do no harm, don’t be an ass.
  • 18. When / How to Double-Down? • When to “follow-on” (write 2nd check): • user/customers are scaling • revenue/profit is increasing • unit economics improving • other experienced investors putting in more money • founders never talk about selling / don’t ask for your money ! • When NOT to double-down: • founders begging you for money • still no product / no revenue / un-profitable • team isn’t shipping product fast / frequent • valuation too high / raised too much money • can’t increase ownership by at least 50-100% • even if making progress; exit still not likely • you have other / better alternatives
  • 19. The Flat, The Elbow, The Wall • Invest @ “The Flat” when prices are low Good Shit • Double-down if/when Happening Startup W you detect “The Elbow” (if valuation isn’t crazy) ! • Don’t invest @ “The Wall” unless capital is “The Elbow” infinite — if valuation starts running away, you usually can’t buy any meaningful ownership relative to existing. Time Startup L Startup K “The Flat” “The Wall” 3 2 1 3
  • 20. Questions? Comments? • More? – http://500.co (our company) – http://500hats.com (my blog) – https://angel.co/500startups (our fund) – Dave McClure, @DaveMcClure