Don’t get swept away by success 🌊

Welcome back to another edition of The Wise Exit!

In today’s newsletter: 

• 3 lessons from Alexa von Tobel about her exit from LearnVest 👩🏼‍💻

• A brand new episode of the Cashing Out podcast 🎧

• Our round-up of interesting M&A transactions from the past week 💰

Let’s dive in!

Alexa von Tobel was only 24 years old when she walked into the admissions office at Harvard Business School to inform them she was taking a leave of absence. It was the beginning of the recession in 2008 and she had made a gut decision to start her own company.

With a 75-page business plan in her pocket, which she had written the year before while working as an analyst at Morgan Stanley, von Tobel started sharing her idea with venture capital and angel investors. She raised over $1 million within a year (and almost $75 million over 4 years). 

Her company, LearnVest, is an online financial advisory firm offering free and approachable financial planning tools and the ability to connect with a certified financial planner. She sold the company to Northwestern Mutual for $375 million in 2015, considered one of the biggest fintech acquisitions of the decade.

Von Tobel now manages her new company, Inspired Capital, a $500+ million early-stage venture capital firm. Below are lessons she’s learned from being a founder and selling her first company.

M&A Lesson 1: “Very healthy paranoia”

Von Tobel had immediate success with LearnVest. On launch day, thousands of people tried to sign up for her services on the website, crashing it temporarily. But she didn’t get swept away by it, not then and not when she was up to 1.5 million users. 

“No good entrepreneur ever really is like, ‘[Everything] is awesome,’” von Tobel says. “You’re always in a good state of very healthy paranoia.”

Her general business advice of not getting swept away by successes also holds true when planning for an exit. The M&A process doesn’t usually go exactly as planned, so a more cautious approach can mitigate against overestimating any one success.  

M&A Lesson 2: Have a learning mindset

In many interviews, von Tobel talks about the importance of always learning new things. And then to be okay with being wrong. 

Learning how to run a business is important but so is the learning mindset itself: being okay with failing, learning something from it, and leaning into the biggest challenges. 

She says that once you start building this resilience, you begin trusting your own skill sets. And that is what makes a great entrepreneur.

M&A Lesson 3: Stay in touch

Relationships are so important when building, growing and selling a business that von Tobel has a phrase she uses called, “the artful fineness of staying in touch.” It’s a fine balance between being annoying and being persistent.

She advises that someone saying ‘no’ today doesn’t mean it can’t be a ‘yes’ tomorrow. Some of her early investors in LearnVest said ‘no’ at the beginning but changed their mind later.

So find ways to stay in touch with the people you meet along the way, as they can become supporters, investors or even buyers down the road.

Cashing Out: How To Build A Proper Succession Plan For Exit 

Christine Nicholson sold her first business after 1 year. She then helped a family office sell over 40 businesses. Today, she runs Get Exit Ready, acting as a business mentor to those who need help with succession planning before the sale of their businesses.

In this episode, Christine talks about:

• The three things that every founder needs to focus on when building their business

• The difference between exit planning and succession planning

• What a perfect succession plan look like

M&A News 📰

• Hospitality: Airbnb acquires AI startup Gameplanner.AI for just under $200 million.

• Automotive: Volvo to acquire zero-emission battery business Proterra for $210 million.

• Confectionary: Mars' $662 million acquisition bid sends shares of Britain's Hotel Chocolat soaring 160%.

• Blockchain: Under new leadership, Terraform Labs acquires cross-chain analytics firm Pulsar Finance.

That’s all for now. 

Tune in next Wednesday for another set of M&A lessons, and have a great rest of the week. 👋