The venture capitalist's job can be rewarding -- but it's hard work. VCs must find great entrepreneurs with big ideas, compete with other VCs to convince their partners to invest, close an investment deal on reasonable terms, and serve on a startup's board -- offering the guidance the entrepreneur needs to scale the startup to a successful exit.

Earlier this month I interviewed one such VC -- Salil Deshpande, Managing Director of Bain Capital Ventures in Palo Alto, Calif. Before joining Bain Capital in 2013, Deshpande earned a B.S. in Electrical Engineering from Cornell and an M.S. from Stanford in the same subject. He was a software engineer, started a middleware company, and became a venture capitalist.

Here are three of what I think are his most noteworthy investments:

  • Dynatrace. As Desphande explained, "We found this company in Linz, Austria when it was just engineers, pre Series A. We invested, left R&D in Linz, where they were successfully recruiting stellar engineers from the local university, and built go-to-market in Boston. We hired a CEO, John Van Siclen to run the company. It worked beautifully. We sold the company to Compuware. It's been spun out as an independent company again, with $500M in revenue, and John Van Siclen still running it!"
  • MuleSoft. "I invested from my prior firm, Bay Partners. Company was founded in Malta. A bunch of engineering and R&D was then moved to Argentina. Go-to-market was built in San Francisco, hired Greg Schott as CEO, company went public, trading at a $3 billion market cap," he said. As of August 17, Mulesoft was valued at $2.7 billion.
  • Redis Labs. "The open source software was created by a reclusive founder who lives in Sicily. R&D and engineering lives in Tel Aviv. Go-to-market was built in Mountain View, where we hired a strong chief revenue officer (CRO) and chief marketing officer (CMO). The company is a rocket ship," said Deshpande.

Two things struck me about his investments -- he offers an interesting perspective on the strengths and weaknesses of Silicon Valley as a place for startups compare to other regions and he has helped many CEOs by giving them useful advice.

He points out that Boston and Silicon Valley have many pillar companies -- which are local, publicly-traded companies that supply capital and talent to startups and use their products. Silicon Valley's pillar companies are well-known ones like Google, Apple, Facebook and so on. In Boston, he said, the pillars include "HubSpot, Logmein, Tripadvisor, Wayfair, and Akamai Technologies."

Pillar companies are a source of engineers and so-called go-to-market (GTM) talent. "The pillar companies are indeed a good supply of engineers - and Bay Area engineers tend to be sophisticated, seasoned and mature. This is partly because of the size, scale and sophistication of the technical problems these companies need to solve, which are unlike problems other types of companies need to solve," said Deshpande.

Pillar companies develop entrepreneurial talent for a region. As he said, "They end up being excellent training grounds for engineers, and sowing the seeds of new startups. For example, Netflix had created something called Spinnaker to mange deployments to their complex infrastructure. They recently open sourced this, and Google endorsed it and committed to support it too. And I (Bain Capital Ventures) funded the company."

Bain Capital locates where the GTM talent resides. "We are in Boston, New York and San Francisco because those are the best places to build GTM operations -- which includes sales leadership, marketing leadership, product management and related activities," he said.

Because their mind-blowingly high pay scales, investors are looking outside those regions for engineers As Desphande said, "These places no longer have the best cost-benefit for building engineering and R&D teams. The San Francisco area and Boston certainly used to be. But now, to use a term from the Uber app, we are in 'surge pricing' for engineers because everybody from the mega caps (like Google, Facebook, Apple, Netflix, etc.) down to the plethora of Series A through E, soaks up that talent aggressively. We have found a reliable pattern where engineering and R&D can be elsewhere in the US, or Western or Eastern Europe, and we build go-to-market operations in either San Francisco, Boston, or NYC. Engineering teams that are not located in the Bay Area can be the more stable, more loyal, less expensive, and less poachable by Google, Apple, and Facebook"

One thing Silicon Valley does well is to provide strong mentor networks. "Mentors tend to be sales leaders, marketing leaders, and engineering leaders are the pillar companies, and also angels. All prior success feeds right back into the ecosystem. It's big now but I see it just getting bigger and bigger. This is partly why we recently announced a program where we set up these mentors as "scouts" with their own seed funds," he explained.

Bain Capital has an effective way of helping its portfolio companies to grow. As Desphande said, "We proactively partner with our portfolio companies and have a huge global network that we draw upon to help our companies scale."

Before joining Bain Capital, Deshpande's firm invested in a buyer behavior analytics company called TeaLeaf which IBM acquired in 2012. Its founder and CTO, Robert Wenig, praised Deshpande's two plus years of service on the company's board.

According to Wenig, "Salil was active, responsive, proactive, and a big proponent of growing faster and finding adjacent markets, and eventually driving to an exit. Salil attended our user conferences and customer training sessions so that he could understand our products deeply, which I've rarely seen investors do. Since he was an active early-stage investor in our space, he routinely found early stage companies with whom we had synergy. Salil connected us with probably a dozen companies which were good acquisition candidates for us. We engaged with three to five of them, and acquired one."

This is one of many types of mentoring that entrepreneurs find valuable -- here are some others. The takeaway for founders is to find an investor who can provide capital and mentoring to help you grow.