Toby Clarence-Smith, Valuation Expert in Milan, Metropolitan City of Milan, Italy
Toby Clarence-Smith

Valuation Expert in Milan, Metropolitan City of Milan, Italy

Member since August 25, 2016
With over a decade of experience across private equity, venture capital, and banking, Toby founded and successfully sold a venture-backed eCommerce company, giving him a unique skill set that combines the financial/investment perspective with tangible operational expertise. His consulting work focuses on helping clients with diligence investment opportunities, as well as companies looking to raise capital and grow their businesses.
Toby is now available for hire


Select Certifications

Industry Expertise

  • Advertising & Marketing
  • Finance
  • Venture Capital & Private Equity
  • Retail
  • eCommerce
  • Financial Modeling
  • Project Management
  • Startups

Software Expertise

Other Expertise


  • Founder & Managing Partner

    2019 - PRESENT
    CS Investimenti
    • Focused efforts on deal origination, assessment, and due diligence to find one single SME to acquire and then actively manage.
    • Built detailed cashflow models for multiple investment opportunities to assess intrinsic cashflow generation through both up and down cycles.
    • Negotiated with business owners regarding the structure of acquisitions including earn-out mechanisms, seller note issuance, and layered financing structures.
    • Industry assessment and sector-focused macro predictions to choose specific verticals in which to focus the search.
    Focus areas: Valuation, Financing, Small & Medium-sized Enterprises (SME), Mergers & Acquisitions (M&A), Due Diligence, Private Equity
  • Venture Capital Investor

    2016 - 2017
    Mountain Nazca
    • Acted as an entrepreneur-in-residence, assisting portfolio companies with operational issues and growth-related challenges.
    • Participated as a member of the investment team. I aided in the origination of new dealflow and assessment of investment opportunities.
    • Helped develop thesis-based investment strategies around global macro trends and sectors. Areas of focus; cryptocurrency, fintech, and online commerce and marketplaces.
    • Assisted with fundraising efforts for the new fund, helping put together the pitch and other fundraising-related documentation.
    • Spearheaded the development of a new investment strategy akin to "company building" but where the original focus was on the entrepreneur rather than the idea itself.
    Focus areas: Venture Capital, Startups, Growth Capital Raising, Fundraising, Mergers & Acquisitions (M&A), Technology
  • Co-Founder | CEO

    2013 - 2016
    • Launched one of the most respected and successful startups in the country, receiving multiple rounds of investment from the top venture capital funds in the country.
    • Built an extremely loyal customer base with incredibly high net promoter scores.
    • Oversaw an expansion from a three-person team to a 50+ person team.
    • Managed the entire development of the technology platform across web, mobile web, and native mobile applications.
    • Opened our first retail store to build out a full-service omni-channel retailer.
    • Built all the operating and financial models underlying three rounds of capital raise with Venture Capital funds as well as business plan approval at the board level.
    Focus areas: Financial Reporting, Venture Capital, Fundraising, eCommerce, Business Intelligence (BI), Digital Strategy, Marketing, Technology, Retail & Wholesale
  • Founder Intern

    2012 - 2012
    • Led the opening of a warehouse from which we were processing over 1,000 orders a day.
    • Led and managed a UX/UI review with clients and delivered several recommendations to the product team regarding improvements to the platform.
    • Modeled and proposed an optimized customer service team structure.
    • Managed an offline marketing strategy (below the line) for a project.
    • Offered a full-time founder position by the end of my time at Linio, but decided to turn it down to launch my own company.
    Focus areas: Operations Analytics, eCommerce, Customer Service, Marketing, Retail & Wholesale
  • Investment Associate

    2010 - 2010
    Bridges Ventures
    • Helped prepare the investment memorandum for an investment in a chain of gyms.
    • Oversaw incoming business plan proposals and appraisals.
    • Built a detailed store rollout financial and execution model for one of the portfolio companies.
    • Helped develop the social impact assessment framework.
    Focus areas: Entrepreneurship, Social, Venture Capital
  • Investment Banking Assistant Vice President

    2007 - 2010
    Barclays Capital
    • Prepared investment memorandums and credit memos for highly leveraged transactions.
    • Managed portfolios and assessments of loan book portfolios.
    • Created a pitch book for corporate finance and M&A deals.
    • Did extensive valuation and merger analysis.
    • Managed client responsibilities with some of the world's largest private equity funds.
    • Promoted six months early (a highly unusual occurrence).
    Focus areas: Valuation, Financial Modeling, Mergers & Acquisitions (M&A), Corporate Finance, Debt Structuring, Leveraged Finance

Other Experience

  • The Most Exciting Asset Class in Private Equity? Search Funds From the Investor’s Perspective (Publication)
    In the current low interest rate environment, investors have been increasingly moving towards alternative asset classes, particularly private equity which continues to attract the lion’s share of investor capital. But could a relatively unknown, niche new asset class hold the key for outsized market performance? In this article, Toptal Finance Expert Toby Clarence-Smith uncovers the world of search fund investing, reviewing some of the key aspects of the asset class from the investor standpoint as well as running through the main benefits of putting money to work in this space.
  • Don't Scale an Unprofitable Business: Why Unit Economics (Still) Matter (Publication)
    With venture funding having grown more than 120% in the US in the last five years, startup founders and investors alike have grown increasingly comfortable with low margin business models. But the successes of the Amazons and Facebooks of this world often mask failure in a slew of other sectors, where the "build it and they will come" model doesn't always work. In this article, Toptal Finance Expert Toby Clarence-Smith brings attention back to the importance of studying a business’ long-term sustainability prospects, with a particular focus on unit economics, one of the building blocks of profitability and breakeven analysis for startups.
  • Amazon vs. Walmart: Bezos Goes for the Jugular With Whole Foods Acquisition (Publication)
    Through its acquisition of Whole Foods, Amazon is not only likely to disrupt the grocery shopping experience but is perhaps embarking on a grander push that could change the entire retail landscape, leaving Walmart on the back foot.
  • Has the US Equity Crowdfunding Market Lived up to Expectations? (Publication)
    Four years on from the signing of the JOBS act, equity crowdfunding remains a small, niche market. In this article, we take a look at the current state of equity crowdfunding in the US and assess some of the challenges the market faces if it wants to grow into its potential.
  • Since the historic Brexit vote, much speculation has been made regarding the effects this would have on the UK's economy. In this article, I take a look at what the anticipated impacts of Brexit on the UK financial sector are, assess their merits and likelihood, and see what the long-lasting impact on the financial sector around the world may be.
  • The Party Isn’t Over: A Deep-Dive into Why Unicorns Will Bounce Back in 2017 (Publication)
    Between 2013 and 2015, the number of Unicorns exploded to 140 members, marking an incredible growth spurt in valuations and positive sentiment toward the venture industry. But after a rocky 2016, in which scandals, funding downrounds, and more cautious investor commentary emerged, many have questioned the validity of the sector’s valuations. With this backdrop, 2017 is shaping up to be a make-or-break year for the Unicorn Club. Is the party over?


  • Master of Business Administration (MBA) in Finance
    2010 - 2012
    The Wharton School of the University of Pennsylvania - Philadelphia, PA, USA
  • Bachelor of Science in Economic History (Economics)
    2004 - 2007
    London School of Economics and Political Science - London, England


  • Endeavor Entrepreneur
  • GMAT: 760
    Graduate Management Admission Council

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