100 Lessons Learned From Entrepreneurs That Have Built Billion Dollar Companies

We recently celebrated producing over 100 episodes of the Dealmakers Podcast. where some of the most successful entrepreneurs share how they did it. During this process, I have collected the most important lessons learned from entrepreneurs that have built billion dollar companies.

On the podcast, we’ve featured many great entrepreneurs and investors who have raised hundreds of millions for their startups as well as many that have exited for $1B. These are some of the key takeaways…

1) Stay humble, and they are

2) Stick with it, keep your eye on the end game

3) The worst that can happen is you have to get a job again

4) It’s about people 

5) It’s all about culture 

6) Culture is a competitive advantage

7) It’s not for the money. The first company Mohit Aron built is worth $7B and the second one $1B.

8) An exit isn’t just about cashing out

9) You never stop growing

10) It can be smarter to hire an outside CEO. This allowed Daniel Cane to sell Blackboard for $1.6B.

11) Be careful who you pick as investors

12) Raising money is about relationships is one of the constant patterns when I was thinking about the lessons learned from entrepreneurs that have appeared on the podcast. 

13) You’re never too young to start

14) You’re never too old to launch another startup. Joe DeSimone was 50 and his business is worth now $2.5B.

15) Early retirement doesn’t work for entrepreneurs

16) Entrepreneurship is addictive

17) Money costs more than the interest

18) Investors can bring a lot more value than the money

19) You can bootstrap a really big company

20) Now all your employees can work remotely. Sid Sijbrandij built GitLab into a $1B business with all 700 employees working remotely.

21) Fundraising can take years but it doesn’t have to

22) Develop your network years before you need it

23) There are a lot more billion dollar companies that exit than you probably realize

24) A good college can pay big dividends in a valuable network

25) You can build a great company with your family. Ben Uretsky and Mosey Uretsky built Digital Ocean into a $1B business. 

26) Successful people enjoy sharing with others

27) Starting a company and growing it, is never, ever easy

28) Take time out with family now, tomorrow is never promised

29) One of the greatest rewards of a big exit is what it does for your team

30) If you love problem-solving entrepreneurship is for you. Kristo Käärmann saw the problem with transferring money overseas and that led him to build a $3.5B company. 

31) There is always more to learn

32) It doesn’t matter where you come from and how little you start with

33) Cold emails still work for fundraising 

34) Ideas are cheap, it’s all about the execution

35) Having a unique distribution channel is a massive advantage

36) Nothing works until you’ve got product-market fit

37) Big businesses aren’t as evil as you think, once you sell to one

38) The cliche about big businesses being too slow and lost in red tape are still true

39) Long earn-out periods in acquisitions rarely work

40) Second and third startups aren’t always easier, nor a guaranteed success

41) For fast-growth companies, local capital partners can make expansion easier

42) Most M&A deals don’t last, but they can

43) Innovate or die

44) Don’t rely on one strategic partner or channel for your success. David Karandish sold Answers.com for $900 million but the company almost died when Google changed its algorithms on search.

45) Your unique vision and application, is more valuable than the idea, just as these Uber and WeWork competitors have proven

46) Most repeat entrepreneurs still raise outside money, even if they can afford not to

47) Delayed gratification really pays off

48) Nothing stays impossible when great teams let themselves dream big. Reggie Aggarwal had over 100 employees. He had to let all of them go except for 15 of them. He recently sold Cvent for 

49) Private equity seems to be taking more public companies private again

50) Your first startup probably won’t be your last

51) You can’t be discouraged by investor rejection, some like Henry Ward have faced 300 no’s to build a $1B business 

52) It doesn’t matter how much you start with, whether it’s $800 in your pocket or going $200k in debt to make it work

53) When it comes to exits, everything is negotiable

54) Entrepreneurs often become angels themselves like Fabrice Grinda. So far he has invested in over 400 startups.

55) Taking plenty of time to think and hone your idea is worth it

56) There’s little that can’t be accomplished when you are committed to the mission

57) A great M&A advisor can bring a lot of value

58) The first offer you get for your startup probably isn’t the best one. Josh Abramson declined a $9 million acquisition offer at age 18 when he was in the process of building Vimeo.

59) Being the head of a public company is a different ball game to being a founder. Jay Chaudry built five companies and knows this well with his last one valued at $10B.

60) Silicon Valley is still alluring but you can do just fine launching your startup somewhere else

61) Everything is always changing

62) Talk to your customers often was another repeating pattern when looking back at those lessons learned from entrepreneurs

63) A can be a great time to start a business

64) It’s a lot easier to raise money when you’re not in a recession

65) Take the money while it’s on the table, it may not be there tomorrow

66) You can build a multi-million dollar revenue business in less than 2 years. Michael Cammarata did it at age 13. 

67) Great investors flock together

68) Make sure you are in a really big market. Jeff Raider took this to heart and built not one but two billion dollar companies with Warby Parker and Harry‘s.

69) Corporate partnerships can be a great gateway to an exit

70) You can build businesses designed to get bought

71) You can create a very content-rich podcast in a very short period of time, with the right introductions

72) More successful founders use LinkedIn and email than any other communication tools

73) It’s really hard to go work for someone else, after the freedom of your own business

74) Going to work with others is a great way to learn from the inside. Gene Berdichevsky was employee #7 at Tesla and then went out to build a $1B business. 

75) Successful founders are generous. This was one of the surprising lessons learned from entrepreneurs that have built billion dollar companies. If you are greedy the chances are slim to none when thinking about reaching the top of the mountain. It is a long steep battle and you need people that are loyal and well rewarded along the way.

76) Successful entrepreneurs are good at listening to feedback

77) You can never do it all alone

78) The best entrepreneurs empower their teams and get out of their own way

79) Top entrepreneurs love to read

80) Surviving exit due diligence is rarely fun or fast

81) Agreeing to an exit is rarely just about what the founders get paid

82) Billion dollar companies are still often born in garages and cramped studio apartments. Just ask Jyoti Bansal as he recently sold his business for $3.7 billion

83) A great legal team is a good early investment

84) Strategic acquisitions can often justify billion-dollar valuations

85) Companies are bought not sold, but you have a lot of influence over the appetite for and price of your business

86) The IPO roadshow can be fun, but anti-climatic

87) Great books can still be a game-changing factor in motivating to success

88) Startups are raising more and more rounds of funding, a Series E is no longer uncommon

89) Most of the best startups are born out of personally experiencing inefficiencies in the market

90) The most mature industries are some of the most vulnerable to disrupt

91) Your brand can be more valuable than your business looks on a P&L sheet

92) A roll-up of the industry is common before a large acquisition or going public. Daniel Saks used the acquisition spree strategy to build a $1B business. 

93) Starting out in a consulting firm or investment bank is a common first job before launching a startup

94) Most successful entrepreneurs focus on flying the business, not grabbing a parachute and looking for the nearest exit

95) Travel and quality time with family are the top luxuries successful entrepreneurs splurge on when they achieve big exits

96) How we handle our health is going to change a lot in the next few years

97) No one regrets becoming an entrepreneur, no matter how hard it is

98) Fundraising is a lot more efficient when you shortlist the best fitting investors first

99) For immigrants, America is still very much the land of opportunity, and it’s a good thing for America too. Many of those lessons learned from entrepreneurs were from those that were immigrants. 

100) You can win by having a big piece of a medium-sized company, or a small piece of a really big one

101) There is a lot to be learned from following the journeys of other successful founders

102) Don’t rely on just one main investor or funding source

103) Don’t underestimate how long it may take for your market to mature, you don’t want to be too far ahead

104) Make sure your market isn’t already peaking

105) Hiring a recruiter can be one of the best first hires

106) Be patient, there are a lot of twists and turns coming, but you’ll get there in the end

107) You’ll never know if the next ask is the yes if you don’t try one more time

108) Even the most talented and successful founders have to deal with friends and family doubting them and thinking they are crazy in the beginning

109) When an investor offers you $1B or nothing, you take the money, even if just to stop it from going to your competition

110) Cannabis is a much more sophisticated and political business than you might expect

111) Real entrepreneurs don’t last long in big corporate giants

112) Big companies are increasingly finding it more efficient to buy new tech than develop it

113) You need to be just as in tune with the direction of capital markets as your own market

114) You can’t count on funding and today’s terms to be available tomorrow

115) As a founder you have to keep your pace of personal growth ahead of how fast your company is growing

116) More companies are seeing the US as their main market on the world map, and they are moving here

117) You can still raise money on an idea on a napkin and a great team, but the odds aren;t in your favor

118) We could once again be on track to see a lot of consolidation in tech, especially fintech and retail

119) Canadian entrepreneurs can still be better off launching in the US first

120) Sometimes you just need to quit your job to prepare to get ready to be an entrepreneur

121) Highly successful founders often start at least three businesses, and most aren’t done yet

122) Data, insurance, cybersecurity, and food are some of the biggest spaces being funded today

123) Plans are far less valuable than just digging in and breaking things down

124) The best entrepreneurs are thinking far bigger and longer than most ever allow themselves to imagine

125) Starting a business with family can really work out well

126) Startup accelerators can pack a lot of value, but the best are harder to get into than Harvard

127) Rules are made to be broken

128) Marketing is often the missing piece for technical founders

129) Storytelling makes all the difference

130) Picking investors is more like recruiting and vetting a team 

131) Putting yourself in the investors’ shoes and mind can go a long way

132) It’s always obvious you had a brilliant idea, 10 years after you start

133) Working in other startups can be a great way to learn prior founding your own

134) The majority of the most successful startups are started by older founders

Summary

Successful entrepreneurs have a lot of value to offer new founders. They’ve been where you are and where you are going. There will always be trial and error and testing to do. Yet, learning from these individuals can help shorten the path to success, elevate your potential, and take a lot of pain out of the journey.=

So, how do you learn from them?

1. Listen to the Dealmakers Podcast every week for new shows
2. Connect with them on Twitter and LinkedIn (our shows include their social handles)
3. Read their books and blogs
4. Hangout where they hangout
5. Go work for them until you are ready to go out on your own
6. Pitch those who are now angel investors and are leading funds
7. Invite them to be your cofounders or advisors
8. Ask for introductions from your investors and advisors

At the end of the day, storytelling is everything when building a meaningful business. This is applied to fundraising, attracting customers, or building partnerships. Being able to capture the essence of what you are doing in 15 to 20 slides is the key.

For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted. Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here).

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

[emaillocker id=693]ACCESS THE PITCH DECK TEMPLATE[/emaillocker]