There are a lot of words used to describe SoftBank’s ruthless leader Masayoshi Son, but I never thought “embarrassed” would be one of them.

In a new interview, Son laments his investing record. “The results still have a long way to go and that makes me embarrassed and impatient,” Son said in an interview with Nikkei Business. “I used to envy the scale of the markets in the U.S. and China, but now you see red-hot growth companies coming out of small markets like in Southeast Asia. There is just no excuse for entrepreneurs in Japan, myself included.”

Son built a $13.8 billion personal fortune by transforming SoftBank into a global technology conglomerate and reaping massive returns from investments like Alibaba. The $100 billion Vision Fund has stakes in some of the largest, most important tech companies. But it’s also haunted by two of its troubled marquee investments: Uber and WeWork. Uber’s share price has suffered a more than 30% drop from the level at which the company went public, and WeWork is still reeling from the loss of its CEO as the market balked at its inflated valuation and shaky governance. That’s not great news for SoftBank, which is trying to woo investors and raise capital for its second mammoth Vison fund.

Here’s the thing though: If you’ve followed Son for long enough, you know that this isn’t where the story ends. In his eyes, he has plenty of time. WeWork and Uber may be losing money now, but they will be substantially profitable in 10 years’ time, Son said in the interview.

Two years ago, I discovered a 2010 SoftBank deck, which has since been taken down from the website. It outlines the Japanese behemoth’s 30-year vision, and it gives an interesting glimpse of Son’s ruthless ambitions. Son has a 300-year view of SoftBank’s growth strategy, and he’s industry-agnostic, betting on information and data instead. But his company’s shares have been battered by more immediate concerns, now trading at close to 31% lower than they were in April.

To me, the most shocking thing in the whole SoftBank saga is that it appears as though the risk-loving investor is changing his tune when speaking to founders. He famously told former WeWork CEO Adam Neumann that he appreciated how he was crazy—but thought that he needed to be crazier. “Recently, I’ve been telling founders to ‘know your limit,’” Son said in the interview. “Knowing your limitations will help unleash limitless possibilities.”

Read more.

INSURANCE IS (STILL) SEXY: I wish I was as good at playing the lottery as I am at predicting weird, super niche VC trends. Remember when I put my entire reputation on the line and called insurance “sexy?” Well, we have another insurance startup joining the unicorn club.  

Next Insurance, a Palo Alto, Calif.-based based firm that sells insurance products to small businesses, raised $250 million in Series C funding at a $1 billion valuation. The investor was Munich Re. It will use the capital to build new products and expand its customer initiatives.

The new funding mints Next Insurance as the fifth unicorn in the insurance tech category, joining Root Insurance ($3.65 billion), Lemonade (valued at $2 billion+), Clover Health ($1.2 billion) and Hippo ($1 billion).

VENTURE DEALS

- Tier Mobility, a Germany-based startup that operates electric scooters, raised $60 million in Series B funding. Mubadala Capital and Goodwater Capital co-led the round.

- Tend, a New York-based dental brand, raised $36 million in seed and Series A funding. Redpoint Ventures led the round, and was joined by investors including Tom Lee of OneMedical, Neil Blumenthal and Dave Gilboa of Warby Parker, Zach Weinberg of Flatiron Health, and Bradley Tusk of Tusk Ventures. 

- Osaro Inc, a San Francisco-based provider of machine learning software for industrial automation, raised $16 million in Series B funding. Investors include King River Capital, Alpha Intelligence Capital, Founders Fund, Pegasus Tech Ventures and GiTV Fund.

- Gradient AI, a Cambridge, Mass.-based enterprise software provider of artificial intelligence solutions in the insurance technology space, raised $6 million in Series A financing. Forte Ventures and Sandbox Insurtech Ventures led the round, and were joined by investors including MassMutual Ventures.

- Natalist, a Charleston, S.C.-based women’s health startup focused on fertility, raised $5 million in seed funding. Investors include Collaborative Fund, Cowboy Ventures, Fuel Capital, Rock Health, and xFund. 

- Oneiro, a Boston-based provider of blockchain solutions, raised $5 million in funding, from COSIMO Ventures.

- Modern Acupuncture, a Scottsdale, Ariz.-based acupuncture franchise, raised funding of an undisclosed amount. Investors include Strand Equity and Cameron Diaz.

HEALTH & LIFE SCIENCES DEALS

- Adicet Bio Inc, a Menlo Park, Calif.-based biopharmaceutical company, raised $80 million in Series B funding. Investors include aMoon2 Fund, Regeneron Pharmaceuticals, Inc., Johnson & Johnson Innovation – JJDC Inc, Samsung Venture Investment Corporation, OrbiMed, Novartis Venture Fund and Pontifax.

PRIVATE EQUITY DEALS

- WestView Capital Partners made an investment in Receivable Solutions LLC, a Columbia, S.C.-based provider of revenue cycle management services to hospitals and health systems. Financial terms weren't disclosed.

- Kronos Incorporated, a portfolio company of Hellman & Friedman and The Blackstone Group, acquired Optimum Solutions Inc, a Nashville-based provider of human capital management services and solutions. Financial terms weren't disclosed. 

- Hub International Limited, a company backed by Altas Partners and Hellman & Friedman, acquired ProCorp Financial, a Canada-based boutique benefits and retirement consulting firm. Financial terms weren't disclosed. 

- Capstone Logistics, which is backed by The Jordan Company LP, agreed to acquire MileZero, a Seattle-based software company providing logistics tools to the last-mile delivery industry. Financial terms weren't disclosed. 

- CVC Capital Partners agreed to acquire a minority stake in IronSource, an Israel-based mobile marketing company, for more than $400 million.

- Vestar Capital Partners agreed to make a minority investment in Simple Mills, a Chicago-based baking mix and cracker brand. Financial terms weren't disclosed. 

- Hamilton Robinson Capital Partners recapitalized Tanknology, an Austin-based company focused on underground storage tank testing, inspection and compliance management. Financial terms weren't disclosed. 

- Insignia Capital Group made an investment in Netrush, a Vancouver, Wash.-based digital retail agency. Financial terms weren't disclosed. 

IPOs

- BMG SA, a Brazilian bank, may raise up to 1.6 billion reais ($395 million) in an IPO. The firm plans to offer 103.4 million shares (6.3% insider sold) priced between 11.60 reais and 13.40 reais. Read more.

- PropertyGuru, a Singaporean real estate listing firm, filed a for an IPO in Australia that could raise as much as A$380.2 million ($257 million). TPG Capital and KKR back the firm. Read more.

- Oyster Point Pharma, a Princeton, NJ-based clinical stage biotech focused on ocular diseases, filed for an $85 million IPO. The firm posted a loss of $16.5 million in 2018 and has yet to post a revenue. New Enterprise Associates (32% pre-offering), Versant Ventures (32%) and Invus Opportunities (11.8%). It plans to list on the Nasdaq as “OYST.” Read more.

- Innate Pharma, a Marseille, France-based commercial-stage biotech for cancer antibody therapies, plans to raise $80 million in an IPO of 10.7 million shares priced at $7.50 apiece. The firm posted revenue of €94 million ($103.5 million) in 2018 and income of €3.1 million ($3.4 million). Novo - Nordisk (13.9% pre-offering), MedImmune (9.8%), and Bpifrance (6.9%) back the firm. It plans to list on the Nasdaq as “IPHA.” Read more. 

EXITS

- Nautic Partners sold Custom Window Systems Inc, an Ocala, Fla.-based maker of high-quality windows and doors, to Pella Corporation. Financial terms weren't disclosed. 

- Silver Lake agreed to acquire TEG, an Australia-based live entertainment and ticketing company. Sellers included Affinity Equity Partners. Financial terms weren't disclosed. 

FIRMS + FUNDS

- 83North, an Israel-based venture capital firm, raised $300 million for its fifth fund.