We Sold Our Startup! 70 Lessons From 7 Years as a Venture Backed Startup CEO

blake smith
8 min readSep 18, 2019

We did it! After 7 years, we sold our startup, Cladwell.

Actually — we sold it about a month ago. For the past month, I took some time to just rest and reflect with my family. During that time, I kept on feeling grateful for this treasure trove of lessons that I’ve learned throughout the process, and how I wish I could share it with everyone. These aren’t lessons that I just read in a book, these are lessons that I’ve learned with blood. That’s why I am dying to share them with people.

So…I wrote this article!

Back in 2013, I wrote a post in Entrepreneur Magazine entitled “The Top 10 Lessons Learned in the Trenches of Startup Year 1”. So, to end this season — I want to share my condensed learnings from the entirety of Cladwell’s 7 years: 10 key lessons for each year.

If you want to know more, I also recorded a video with any further explanation or story that is necessary. I’ve linked to each spot in this post if you want to dive deeper.

Here we go!

My Top 70 Lessons In Running Cladwell (By Year)


(In 2013 we raised an angel round of funding and launched our first iteration of our product. I had so much hair!) [Video Link]

1. Nobody ever gets any money from big public pitches. [Click this link to jump to point in video where I describe this lesson]

2. Everyone will give you advice. Pick a couple mentors and stick with them. [link]

3. Talk to your customers constantly. Like, call them. [link]

4. Don’t neglect friends, vacation, family, church…DON’T FORGET TO LIVE! [link]

5. The best brands come from the creator’s personality (and THEN strategy.) [link]

6. Never use volunteers on your startup. [link]

7. What’s the longest you can imagine that it will take to raise money? Double it. How much do you need? Double that too. [link]

8. Celebrate early and often. [link]

9. Don’t network or promote yourself. Just make friends. [link]

10. Have grace with your teammates. [link]


In 2014, we expanded features on website, hired a team, added incremental revenue streams (that failed), and raised an additional Angel round. [link]

1. 10 extra minutes of extra time spent planning could save you >$100K. Think before you build. [link]

2. If you don’t love the new hire now, you never will. [link]

3. Your office space / subleases really make a difference for the team. [link]

4. Investors want to be part of a “moment” when you are raising money. (That’s why they call it MOMENTum). [link]

5. Equity does nothing to actually motivate people. [link]

6. Technical people like to re-write everything: Don’t let them do it. [link]

7. A formal warning is a helpful tool when you’re trying to correct an employee’s recurring bad behavior. [link]

8. Being cheesy is part of being the leader — go above and beyond recognizing great work. [link]

9. The team loves it when the CEO brings a big scary problem to the team. (You don’t have to be the hero and solve it.) [link]

10. The moment a work relationship isn’t working, address it. Do not wait. It won’t get better. [link]


In 2015, we created a Youtube channel for customer acquisition, ran out of money, pivoted business model/customer target, bet the business on a partnership w/ Macy’s and got it! [link]

1. Never, EVER raise money from 1 or 2 investors. You need a BIG pipeline if you want leverage. [link]

2. When backed into a corner, ask the question “if we’re going to die, what would we be proud to die trying?” [link]

3. Sometimes anxiety/sadness can be resolved by addressing your physical habits: exercising, eating, sleeping, going outside, spending time with friends, etc… [link]

4. What you watch on TV shapes your mood. [link]

5. The joy of business success dwindles pretty fast. (The joy of having a child is way better.) [link]

6. Don’t work in a different room than your team. You might focus more, but they need your passion. [link]

7. Giving responsibility is gasoline: a little can accelerate someone’s career, but too much will make an irreversible mess. [link]

8. Wherever possible, get your team to experience what your digital product delivers physically. [link]

9. Hire fantastic people. Literally NOTHING is more important for a company than this. [link]

10. You have a choice: either go insane or journal regularly and honestly. [link]


In 2016, we moved to SF, went through 500 Startups Accelerator, and the team started building our new app while I raised $1.5mil Seed Round [link]
  1. You never get anywhere new without trying something new: (Join an accelerator, go to therapy, etc…) [link]

2. Accelerators advertise their expertise, connections, etc… but it’s ALL about the relationships with other founders. [link]

3. If you are building a digital product, read and follow this book. [link]

4. For your Seed round, pitch 1 VC for every $10K you’re raising. [link]

5. When fundraising, move your VC’s through the same stages of fundraising (1st pitch, partner meeting, due diligence, etc…) together. [link]

6. If you want to raise money, just don’t give up. [link]

7. Your family/children are not a liability or distraction. Your family is your power. [link]

8. Firing someone should take ~10min. Focus on the logistics and give them the dignity of hating you for awhile. [link]

9. If you want to save $90,0000 in legal fees, from day 1 — create a c-corp and set the cap table up on Carta. [link]

10. Leaving your team alone while you raise money is dangerous and causes them damage. [link]


In 2017, we tripled the team, we launched our new app, spent a lot of time on product and scaled marketing at the end of the year. [link]
  1. The LOGISTICS of a product launch can make or break it. [link]

2. As the leader — NEVER--EVER do something that you disagree with. Be open to being convinced, but if you aren’t — DO NOT GO ALONG to protect people’s enthusiasm or protect their feelings. You’re guaranteeing failure. [link]

3. New hires will be a threat to old employees. Do not indulge this fear. Just move ahead. [link]

4. An intern will affect your culture just as much as any other employee. [link]

5. If an employee is having personal problems, clearly communicate what you expect and don’t bend. [link]

6. If you don’t have Product-Market-Fit, immediately stop working on incremental features and improvements. Obsess over the systemic problem. [link]

7. More people does not necessarily = more output. [link]

8. The time to push like crazy is when you have cash in the bank. GO! If you wait to sprint till you’re running out, it’ll be too late. [link]

9. The CEO needs to be obsessed with the core risk facing the business. Do NOT delegate. Do NOT outsource. Get in there and break some eggs. [link]

10. When your team gets bigger, you have to OVER communicate constantly: this is what I’m saying — this is what I’m not saying. [link]


In 2018, we raised a bridge round, fired 3 team members, tested a bunch of business models, and honed in our core product. [link]
  1. Jump in the ocean whenever you see it.[link]

2. If your team’s hearts aren’t together, stop everything and get them back together. [link]

3. The executive team’s personal life MUST be fully taken into account in strategic planning — babies, moving, sickness, etc… This will have a massive effect on the business. [link]

4. You have to FORCE your company to produce the growth chart to raise money. Intellectual honesty isn’t enough to raise a round of funding. [link]

5. NEVER process your doubts with your team. (That’s what friends are for.) [link]

6. Never text anything important to a VC. (Facepalm.) [link]

7. There’s nothing like losing a child to put raising money in perspective. [link]

8. Once you have a really great team, your job is to a) give regular clarity and b) stop talking and let them drive! [link]

9. Never let an external party— investor, partner, etc... be the blocker in an initiative. Never wait. Act now — they can join or not, but you’re moving. [link]

10. Every person has limits. Take a break, or a break will take you. [link]


In 2019 we launched a massive social feature, raised a bridge round to fund the sale process, and sold the company to a group of private investors led by my co-founder. [link]
  1. Don’t communicate back-up plans with the team. It’s plan A or bust! [link]

2. Remote teams are AWESOME until the company hits trouble, then it’s HORRIBLE. (Not sure what to do about this.)[link]

3. Selling a company requires a clear and disciplined process — don’t test waters. Either do it or don’t. [link]

4. In huge successful exits, first money in makes the big bucks. Every other scenario, last money in wins. [link]

5. If you want people to notice you and think you’re important, be a startup CEO. If you want to build wealth, be an investor. [link]

6. Adding lawyers in the mix makes things feel adversarial. It takes a lot to resist it. [link]

7. Don’t tell your team you’re selling the company. [link]

8. Time can accomplish things that emails, phone calls, leverage, pressure can’t do. Let time do it’s job. [link]

9. Examine your investor’s values. Their % of ownership will inevitably become that % of your company’s values. [link]

10. No matter who you are it is a FACT: You will be somewhere, with someone when your relationship with your company ends. Invest in that somewhere and that someone now — you won’t regret it! [link]

— -

That’s it! I hope this was helpful.

If you ever have the chance to start a company, I highly recommend it. It’s scary, painful, embarrassing, and difficult — but it’s grown my trust in God and has taught me a ton.

Thanks for reading. If you’ve read this far and we haven’t met, we should hang out some time! Just reach out at: blake@allsmith.org


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blake smith

CEO of Jumpdocs.com, Former CEO of Cladwell (Exited) / Father of 5/ Husband of 1 / Maker of a mean cocktail. Get coaching @ allsmith.org