Bootstrapping to $5M in Revenue, the Power of Monthly Updates, & the Best Advice for Founders

A newsletter for founders & friends (25th edition)

Hey 👋

Welcome to the 25th edition of Re:VITALIZE, a newsletter with tactics, strategies, and stories on building companies plus cool things we’re seeing in the future of work.

Did you miss last week’s newsletter about a deck for raising $6.5M, term sheet essentials, and the best five-word pitches? Subscribe below so you never miss another👇

---

Top 3 Tweets

🥇 Bootstrapping to $5M in Revenue

adriane schwager @aschwags3

17 months ago, I co-founded my first business Today, we crossed $5,000,000 in revenue with only 5 US full-time employees. Totally bootstrapped I’m a mom, wife, and now a first-time founder/CEO Here are my top 11 learnings on leadership, entrepreneurship, and startups 👇🧵

🥈 The Power of Monthly Updates

yohei.eth @yoheinakajima

In today’s thread, I share the story of our most powerful fundraise tool: the monthly update. We sent: - 27 monthly updates - 594 subscribers - 65.39% open rate - 13.45% click thru How is it powerful? What did we do? Let’s dive in👇👇👇

🥉 The Best Advice for Founders

Some of my favorite responses from this tweet:

Veni Kunche (she/her) @venikunche

@justingordon212 In addition to product-market fit, make sure you have founder-product fit. I think it's easier to stick with it for longer if the business fits into your life and you like running it.

Andrew Gazdecki @agazdecki

@justingordon212 Believe in yourself when others don’t.

Allison Esposito Medina 🇮🇹 @techladyallison

@justingordon212 Have a long outlook and stay focused on that

Daniel Shalinsky @Shalinsky

@justingordon212 Ask yourself if you’re solving a real problem. Seek critical/candid feedback. Customer discovery > almost everything else. And don’t stop doing it. When you think you’ve validated your idea, keep interviewing potential customers.

Christine Carrillo @ChristineCarril

@justingordon212 Figure out if you have a business quickly with the least amount of money possible. Spend a few months, not a year to find product market fit.

Ian Garrett @ianygarrett

@justingordon212 Listen first build second: talk to people that actually have the pain point you're solving for and build based on what you learn instead of building first and hoping they'll like it

Dr. Julie Gurner @drgurner

@justingordon212 Have a long runway...or another source of income (if starting now).

Alexi @kyprianou_m

@justingordon212 Your greatest advantage is your speed. The ability to pivot fast, build fast, launch fast. Don't waste it & take advantage of it while it lasts.

John Otieno @Faddablack

@justingordon212 Here’s what I learned on my journey: 1. Validate the problem before building a product. 2. Choose the right partner to be your co-founder, lack of cohesion between co-founders always spells doom for startups 3. Don’t be afraid of pivoting.

---

Resources

• The FAST agreement for working with advisors

• An ode to cold outreach

• A platform for saving on SaaS subscriptions

• A catalyst for outlier founders

• A platform for improving your company culture

---

Future of Work Reads

• Airbnb Just Accelerated The Future Of Work — Your Organization Can Do The Same (Forbes)

• Web3 Needs In-Person Gatherings (CoinDesk)

• Deepfakes come to remote job interviews (Computerworld)

• The Future of Skills and Learning in a Rapidly Transforming Investment Industry (PR Newswire)

• Even bosses are joining the Great Resignation (Vox)

---

The World of VITALIZE

• This week on The VITALIZE Podcast we had Drew Leahy, the Managing Partner at Hawke Ventures, a firm that recently raised a $25M Fund II.

  • Watch on YouTube

  • Listen on Apple Podcasts or Spotify

• We committed to our 10th investment from VITALIZE Angels

• The VITALIZE family has grown 😊

• Open jobs at Vitalize portfolio companies

---

Future of Work Funding Rounds

• Flexe raised a $119M Series D

  • Flexe delivers omnichannel logistics programs for eCommerce fulfillment, retail distribution, same-day delivery, and network capacity.

  • Top Investors: Alumni Ventures, Tiger Global Management, BlackRock, Acequia Capital (AceCap), Madrona Venture Group

• Mayvenn raised a $40M Series C

  • Mayvenn enables stylists to sell products directly to their clients without the upfront costs and burdens of holding inventory.

  • Top Investors: Andreessen Horowitz, 500 Startups, Goldman Sachs Asset Management, 10x Group, Core Innovation Capital

• Tesorio raised a $17M Series B

  • Tesorio automates accounts receivable management.

  • Top Investors: FundersClub, Y Combinator, Haystack, Madrona Venture Group, Floodgate

• Promoted raised a $6M Seed

  • Promoted helps e-commerce marketplaces achieve profitability by unifying organic search, promotions, and ads in one optimized system.

  • Top Investors: Y Combinator, Rebel Fund, MAGIC Fund, Vela Partners, Preetha Parthasarathy

• Focal Point Procurement Solutions raised a $3M Seed

  • Focalpoint is a procurement modernization startup for businesses.

  • Top Investors: Techstars, Operator Partners, Susa Ventures, Amplo, Surface Ventures

---

Written by Justin Gordon, Director of Marketing at VITALIZE, a venture capital firm and 300+ member angel investing community for everyone investing in U.S.-based B2B software founders in the work revolution. Find us on Twitter, LinkedIn, and YouTube.